Enantioselective deprotometalation of alkyl ferrocenecarboxylates using bimetallic bases
The enantioselective deprotometalation of alkyl ferrocenecarboxylates (FcCO 2 R) using mixed lithium-zinc or lithium-cadmium bases is described. By using FcCO 2 Me as the substrate, chiral lithium alkyl-amidozincates prepared from exo -(α R )- or endo -(α S )- N -(α-phenylethyl)bornylamine ( H- exo...
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| Veröffentlicht in: | New journal of chemistry 2021-12, Vol.45 (48), p.22579-2259 |
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| creator | Dayaker, Gandrath Erb, William Hedidi, Madani Chevallier, Floris Blot, Marielle Gros, Philippe C Hilmersson, Göran Roisnel, Thierry Dorcet, Vincent Bentabed-Ababsa, Ghenia Mongin, Florence |
| description | The enantioselective deprotometalation of alkyl ferrocenecarboxylates (FcCO
2
R) using mixed lithium-zinc or lithium-cadmium bases is described. By using FcCO
2
Me as the substrate, chiral lithium alkyl-amidozincates prepared from
exo
-(α
R
)- or
endo
-(α
S
)-
N
-(α-phenylethyl)bornylamine (
H-
exo
-born-
R
or
H-
endo
-born-
S
) were tested; the best results (27% yield and 62% ee in favor of the
R
P
enantiomer) were obtained by using Bu
2
(
endo
-born-
S
)ZnLi in tetrahydrofuran (THF) at −30 °C before iodolysis. Due to the low compatibility of FcCO
2
Me with alkyl-containing lithium zincates, 1 : 1 mixtures of lithium and zinc amides were tested. Chiral (
H-
exo
-born-
R
or
H-
endo
-born-
S
) or/and achiral (lithium 2,2,6,6-tetramethylpiperidide or lithium diisopropylamide) secondary amines gave good results, the best (81% yield and 44% ee in favor of the
R
P
enantiomer) being obtained by using (
endo
-born-
S
)
3
ZnLi in THF at room temperature. Among other secondary amines also prepared and/or tested, commercial (
S
,
S
)-bis(α-phenylethyl)amine (
H-PEA-
S
) proved promising. After optimization of the reaction conditions, the best enantioselectivity (26% yield and 80% ee in favor of the
R
P
enantiomer) was observed by treating a THF solution of FcCO
2
Me and Zn(PEA-
S
)
2
with Li-PEA-
S
at −80 °C before iodolysis. That no reaction took place with cadmium instead of zinc suggests the formation of 'ate complexes upon treatment of Cd(PEA-
S
)
2
by Li-PEA-
S
while Zn(PEA-
S
)
2
and Li-PEA-
S
would rather work in tandem (Li-PEA-
S
as the base and Zn(PEA-
S
)
2
as the
in situ
trap for the formed ferrocenyllithium). While FcCO
2
Me, FcCO
2
t
Bu and FcCO
2
iPr could be converted into their racemic 2-iodinated derivatives with a yield of 84 to 87% by employing LiTMP (2 equiv.) in the presence of ZnCl
2
·TMEDA (1 equiv.) as an
in situ
trap, their enantioselective deprotometalation rather required Li-PEA-
S
together with Zn(PEA-
S
)
2
to produce the enantio-enriched derivatives with yields of 45-82% and 71% ee.
Our attempts to deprotometalate alkyl ferrocenecarboxylates enantioselectively by using chiral lithium-zinc or lithium-cadmium bases are reported. |
| doi_str_mv | 10.1039/d1nj04526a |
| format | Article |
| fullrecord | <record><control><sourceid>proquest_hal_p</sourceid><recordid>TN_cdi_hal_primary_oai_HAL_hal_03464801v1</recordid><sourceformat>XML</sourceformat><sourcesystem>PC</sourcesystem><sourcerecordid>2609594543</sourcerecordid><originalsourceid>FETCH-LOGICAL-c389t-9be6b590d5c8e2fd5e6b46024b0132813b68778bb7cc9c89cb95a895fbea0983</originalsourceid><addsrcrecordid>eNpVkT1PwzAQhiMEEqWwsCNFYgIpYMcftccKCgVVsHRgs2z3UlLSuNhJof8et0FFTPf13CvdvUlyjtENRkTeznC9QJTlXB8kPUy4zGTO8WHMMaUZYpQfJychLBDCeMBxL3kb1bpuShegAtuUa0hnsPKucUtodKXjpE5dkerqY1OlBXjvLNRgtTfuexPnENI2lPU8NeVuoyptanSAcJocFboKcPYb-8n0YTS9G2eT18enu-Eks0TIJpMGuGESzZgVkBczFkvKUU4NwiQXmBguBgNhzMBaaYW0RjItJCsMaCQF6SdZJxu-YNUatfLlUvuNcrpU83alYmveqgCK4ChKIn_V8e-6-gePhxO17SFCORUIr3FkLzs2PuSzhdCohWt9Ha9ROUeSScp2itcdZb0LwUOxl8VIbU1R9_jleWfKMMIXHeyD3XN_ppEftHuKbw</addsrcrecordid><sourcetype>Open Access Repository</sourcetype><iscdi>true</iscdi><recordtype>article</recordtype><pqid>2609594543</pqid></control><display><type>article</type><title>Enantioselective deprotometalation of alkyl ferrocenecarboxylates using bimetallic bases</title><source>Royal Society Of Chemistry Journals 2008-</source><source>Alma/SFX Local Collection</source><creator>Dayaker, Gandrath ; Erb, William ; Hedidi, Madani ; Chevallier, Floris ; Blot, Marielle ; Gros, Philippe C ; Hilmersson, Göran ; Roisnel, Thierry ; Dorcet, Vincent ; Bentabed-Ababsa, Ghenia ; Mongin, Florence</creator><creatorcontrib>Dayaker, Gandrath ; Erb, William ; Hedidi, Madani ; Chevallier, Floris ; Blot, Marielle ; Gros, Philippe C ; Hilmersson, Göran ; Roisnel, Thierry ; Dorcet, Vincent ; Bentabed-Ababsa, Ghenia ; Mongin, Florence</creatorcontrib><description>The enantioselective deprotometalation of alkyl ferrocenecarboxylates (FcCO
2
R) using mixed lithium-zinc or lithium-cadmium bases is described. By using FcCO
2
Me as the substrate, chiral lithium alkyl-amidozincates prepared from
exo
-(α
R
)- or
endo
-(α
S
)-
N
-(α-phenylethyl)bornylamine (
H-
exo
-born-
R
or
H-
endo
-born-
S
) were tested; the best results (27% yield and 62% ee in favor of the
R
P
enantiomer) were obtained by using Bu
2
(
endo
-born-
S
)ZnLi in tetrahydrofuran (THF) at −30 °C before iodolysis. Due to the low compatibility of FcCO
2
Me with alkyl-containing lithium zincates, 1 : 1 mixtures of lithium and zinc amides were tested. Chiral (
H-
exo
-born-
R
or
H-
endo
-born-
S
) or/and achiral (lithium 2,2,6,6-tetramethylpiperidide or lithium diisopropylamide) secondary amines gave good results, the best (81% yield and 44% ee in favor of the
R
P
enantiomer) being obtained by using (
endo
-born-
S
)
3
ZnLi in THF at room temperature. Among other secondary amines also prepared and/or tested, commercial (
S
,
S
)-bis(α-phenylethyl)amine (
H-PEA-
S
) proved promising. After optimization of the reaction conditions, the best enantioselectivity (26% yield and 80% ee in favor of the
R
P
enantiomer) was observed by treating a THF solution of FcCO
2
Me and Zn(PEA-
S
)
2
with Li-PEA-
S
at −80 °C before iodolysis. That no reaction took place with cadmium instead of zinc suggests the formation of 'ate complexes upon treatment of Cd(PEA-
S
)
2
by Li-PEA-
S
while Zn(PEA-
S
)
2
and Li-PEA-
S
would rather work in tandem (Li-PEA-
S
as the base and Zn(PEA-
S
)
2
as the
in situ
trap for the formed ferrocenyllithium). While FcCO
2
Me, FcCO
2
t
Bu and FcCO
2
iPr could be converted into their racemic 2-iodinated derivatives with a yield of 84 to 87% by employing LiTMP (2 equiv.) in the presence of ZnCl
2
·TMEDA (1 equiv.) as an
in situ
trap, their enantioselective deprotometalation rather required Li-PEA-
S
together with Zn(PEA-
S
)
2
to produce the enantio-enriched derivatives with yields of 45-82% and 71% ee.
Our attempts to deprotometalate alkyl ferrocenecarboxylates enantioselectively by using chiral lithium-zinc or lithium-cadmium bases are reported.</description><identifier>ISSN: 1144-0546</identifier><identifier>EISSN: 1369-9261</identifier><identifier>DOI: 10.1039/d1nj04526a</identifier><language>eng</language><publisher>Cambridge: Royal Society of Chemistry</publisher><subject>Amides ; Amines ; Bimetals ; Cadmium ; catalytic synthesis ; Chemical Sciences ; Chemistry ; chemoselective base ; diastereoselective deprotonative metalation ; directed ortho-metalation ; Enantiomers ; esters ; ferrocenes ; Kemi ; Lithium ; mediated asymmetric-synthesis ; mixed lithium-cadmium ; Optimization ; ortho-lithiation ; planar chiral ; Room temperature ; Substrates ; Tetrahydrofuran ; tmp-zincate ; Zinc chloride ; Zincates</subject><ispartof>New journal of chemistry, 2021-12, Vol.45 (48), p.22579-2259</ispartof><rights>Copyright Royal Society of Chemistry 2021</rights><rights>Distributed under a Creative Commons Attribution 4.0 International License</rights><lds50>peer_reviewed</lds50><oa>free_for_read</oa><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c389t-9be6b590d5c8e2fd5e6b46024b0132813b68778bb7cc9c89cb95a895fbea0983</citedby><cites>FETCH-LOGICAL-c389t-9be6b590d5c8e2fd5e6b46024b0132813b68778bb7cc9c89cb95a895fbea0983</cites><orcidid>0000-0003-3693-8861 ; 0000-0002-2906-2091 ; 0000-0003-4905-1581 ; 0000-0001-9423-995X ; 0000-0002-7482-9351 ; 0000-0002-6088-4472 ; 0000-0002-4982-6589</orcidid></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><link.rule.ids>230,314,780,784,885,27922,27923</link.rule.ids><backlink>$$Uhttps://hal.science/hal-03464801$$DView record in HAL$$Hfree_for_read</backlink><backlink>$$Uhttps://gup.ub.gu.se/publication/310243$$DView record from Swedish Publication Index$$Hfree_for_read</backlink></links><search><creatorcontrib>Dayaker, Gandrath</creatorcontrib><creatorcontrib>Erb, William</creatorcontrib><creatorcontrib>Hedidi, Madani</creatorcontrib><creatorcontrib>Chevallier, Floris</creatorcontrib><creatorcontrib>Blot, Marielle</creatorcontrib><creatorcontrib>Gros, Philippe C</creatorcontrib><creatorcontrib>Hilmersson, Göran</creatorcontrib><creatorcontrib>Roisnel, Thierry</creatorcontrib><creatorcontrib>Dorcet, Vincent</creatorcontrib><creatorcontrib>Bentabed-Ababsa, Ghenia</creatorcontrib><creatorcontrib>Mongin, Florence</creatorcontrib><title>Enantioselective deprotometalation of alkyl ferrocenecarboxylates using bimetallic bases</title><title>New journal of chemistry</title><description>The enantioselective deprotometalation of alkyl ferrocenecarboxylates (FcCO
2
R) using mixed lithium-zinc or lithium-cadmium bases is described. By using FcCO
2
Me as the substrate, chiral lithium alkyl-amidozincates prepared from
exo
-(α
R
)- or
endo
-(α
S
)-
N
-(α-phenylethyl)bornylamine (
H-
exo
-born-
R
or
H-
endo
-born-
S
) were tested; the best results (27% yield and 62% ee in favor of the
R
P
enantiomer) were obtained by using Bu
2
(
endo
-born-
S
)ZnLi in tetrahydrofuran (THF) at −30 °C before iodolysis. Due to the low compatibility of FcCO
2
Me with alkyl-containing lithium zincates, 1 : 1 mixtures of lithium and zinc amides were tested. Chiral (
H-
exo
-born-
R
or
H-
endo
-born-
S
) or/and achiral (lithium 2,2,6,6-tetramethylpiperidide or lithium diisopropylamide) secondary amines gave good results, the best (81% yield and 44% ee in favor of the
R
P
enantiomer) being obtained by using (
endo
-born-
S
)
3
ZnLi in THF at room temperature. Among other secondary amines also prepared and/or tested, commercial (
S
,
S
)-bis(α-phenylethyl)amine (
H-PEA-
S
) proved promising. After optimization of the reaction conditions, the best enantioselectivity (26% yield and 80% ee in favor of the
R
P
enantiomer) was observed by treating a THF solution of FcCO
2
Me and Zn(PEA-
S
)
2
with Li-PEA-
S
at −80 °C before iodolysis. That no reaction took place with cadmium instead of zinc suggests the formation of 'ate complexes upon treatment of Cd(PEA-
S
)
2
by Li-PEA-
S
while Zn(PEA-
S
)
2
and Li-PEA-
S
would rather work in tandem (Li-PEA-
S
as the base and Zn(PEA-
S
)
2
as the
in situ
trap for the formed ferrocenyllithium). While FcCO
2
Me, FcCO
2
t
Bu and FcCO
2
iPr could be converted into their racemic 2-iodinated derivatives with a yield of 84 to 87% by employing LiTMP (2 equiv.) in the presence of ZnCl
2
·TMEDA (1 equiv.) as an
in situ
trap, their enantioselective deprotometalation rather required Li-PEA-
S
together with Zn(PEA-
S
)
2
to produce the enantio-enriched derivatives with yields of 45-82% and 71% ee.
Our attempts to deprotometalate alkyl ferrocenecarboxylates enantioselectively by using chiral lithium-zinc or lithium-cadmium bases are reported.</description><subject>Amides</subject><subject>Amines</subject><subject>Bimetals</subject><subject>Cadmium</subject><subject>catalytic synthesis</subject><subject>Chemical Sciences</subject><subject>Chemistry</subject><subject>chemoselective base</subject><subject>diastereoselective deprotonative metalation</subject><subject>directed ortho-metalation</subject><subject>Enantiomers</subject><subject>esters</subject><subject>ferrocenes</subject><subject>Kemi</subject><subject>Lithium</subject><subject>mediated asymmetric-synthesis</subject><subject>mixed lithium-cadmium</subject><subject>Optimization</subject><subject>ortho-lithiation</subject><subject>planar chiral</subject><subject>Room temperature</subject><subject>Substrates</subject><subject>Tetrahydrofuran</subject><subject>tmp-zincate</subject><subject>Zinc chloride</subject><subject>Zincates</subject><issn>1144-0546</issn><issn>1369-9261</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2021</creationdate><recordtype>article</recordtype><recordid>eNpVkT1PwzAQhiMEEqWwsCNFYgIpYMcftccKCgVVsHRgs2z3UlLSuNhJof8et0FFTPf13CvdvUlyjtENRkTeznC9QJTlXB8kPUy4zGTO8WHMMaUZYpQfJychLBDCeMBxL3kb1bpuShegAtuUa0hnsPKucUtodKXjpE5dkerqY1OlBXjvLNRgtTfuexPnENI2lPU8NeVuoyptanSAcJocFboKcPYb-8n0YTS9G2eT18enu-Eks0TIJpMGuGESzZgVkBczFkvKUU4NwiQXmBguBgNhzMBaaYW0RjItJCsMaCQF6SdZJxu-YNUatfLlUvuNcrpU83alYmveqgCK4ChKIn_V8e-6-gePhxO17SFCORUIr3FkLzs2PuSzhdCohWt9Ha9ROUeSScp2itcdZb0LwUOxl8VIbU1R9_jleWfKMMIXHeyD3XN_ppEftHuKbw</recordid><startdate>20211213</startdate><enddate>20211213</enddate><creator>Dayaker, Gandrath</creator><creator>Erb, William</creator><creator>Hedidi, Madani</creator><creator>Chevallier, Floris</creator><creator>Blot, Marielle</creator><creator>Gros, Philippe C</creator><creator>Hilmersson, Göran</creator><creator>Roisnel, Thierry</creator><creator>Dorcet, Vincent</creator><creator>Bentabed-Ababsa, Ghenia</creator><creator>Mongin, Florence</creator><general>Royal Society of Chemistry</general><general>Royal Society of Chemistry [1987-....]</general><scope>AAYXX</scope><scope>CITATION</scope><scope>7SR</scope><scope>8BQ</scope><scope>8FD</scope><scope>H9R</scope><scope>JG9</scope><scope>KA0</scope><scope>1XC</scope><scope>VOOES</scope><scope>ADTPV</scope><scope>AOWAS</scope><scope>F1U</scope><orcidid>https://orcid.org/0000-0003-3693-8861</orcidid><orcidid>https://orcid.org/0000-0002-2906-2091</orcidid><orcidid>https://orcid.org/0000-0003-4905-1581</orcidid><orcidid>https://orcid.org/0000-0001-9423-995X</orcidid><orcidid>https://orcid.org/0000-0002-7482-9351</orcidid><orcidid>https://orcid.org/0000-0002-6088-4472</orcidid><orcidid>https://orcid.org/0000-0002-4982-6589</orcidid></search><sort><creationdate>20211213</creationdate><title>Enantioselective deprotometalation of alkyl ferrocenecarboxylates using bimetallic bases</title><author>Dayaker, Gandrath ; Erb, William ; Hedidi, Madani ; Chevallier, Floris ; Blot, Marielle ; Gros, Philippe C ; Hilmersson, Göran ; Roisnel, Thierry ; Dorcet, Vincent ; Bentabed-Ababsa, Ghenia ; Mongin, Florence</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c389t-9be6b590d5c8e2fd5e6b46024b0132813b68778bb7cc9c89cb95a895fbea0983</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2021</creationdate><topic>Amides</topic><topic>Amines</topic><topic>Bimetals</topic><topic>Cadmium</topic><topic>catalytic synthesis</topic><topic>Chemical Sciences</topic><topic>Chemistry</topic><topic>chemoselective base</topic><topic>diastereoselective deprotonative metalation</topic><topic>directed ortho-metalation</topic><topic>Enantiomers</topic><topic>esters</topic><topic>ferrocenes</topic><topic>Kemi</topic><topic>Lithium</topic><topic>mediated asymmetric-synthesis</topic><topic>mixed lithium-cadmium</topic><topic>Optimization</topic><topic>ortho-lithiation</topic><topic>planar chiral</topic><topic>Room temperature</topic><topic>Substrates</topic><topic>Tetrahydrofuran</topic><topic>tmp-zincate</topic><topic>Zinc chloride</topic><topic>Zincates</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Dayaker, Gandrath</creatorcontrib><creatorcontrib>Erb, William</creatorcontrib><creatorcontrib>Hedidi, Madani</creatorcontrib><creatorcontrib>Chevallier, Floris</creatorcontrib><creatorcontrib>Blot, Marielle</creatorcontrib><creatorcontrib>Gros, Philippe C</creatorcontrib><creatorcontrib>Hilmersson, Göran</creatorcontrib><creatorcontrib>Roisnel, Thierry</creatorcontrib><creatorcontrib>Dorcet, Vincent</creatorcontrib><creatorcontrib>Bentabed-Ababsa, Ghenia</creatorcontrib><creatorcontrib>Mongin, Florence</creatorcontrib><collection>CrossRef</collection><collection>Engineered Materials Abstracts</collection><collection>METADEX</collection><collection>Technology Research Database</collection><collection>Illustrata: Natural Sciences</collection><collection>Materials Research Database</collection><collection>ProQuest Illustrata: Technology Collection</collection><collection>Hyper Article en Ligne (HAL)</collection><collection>Hyper Article en Ligne (HAL) (Open Access)</collection><collection>SwePub</collection><collection>SwePub Articles</collection><collection>SWEPUB Göteborgs universitet</collection><jtitle>New journal of chemistry</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Dayaker, Gandrath</au><au>Erb, William</au><au>Hedidi, Madani</au><au>Chevallier, Floris</au><au>Blot, Marielle</au><au>Gros, Philippe C</au><au>Hilmersson, Göran</au><au>Roisnel, Thierry</au><au>Dorcet, Vincent</au><au>Bentabed-Ababsa, Ghenia</au><au>Mongin, Florence</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Enantioselective deprotometalation of alkyl ferrocenecarboxylates using bimetallic bases</atitle><jtitle>New journal of chemistry</jtitle><date>2021-12-13</date><risdate>2021</risdate><volume>45</volume><issue>48</issue><spage>22579</spage><epage>2259</epage><pages>22579-2259</pages><issn>1144-0546</issn><eissn>1369-9261</eissn><abstract>The enantioselective deprotometalation of alkyl ferrocenecarboxylates (FcCO
2
R) using mixed lithium-zinc or lithium-cadmium bases is described. By using FcCO
2
Me as the substrate, chiral lithium alkyl-amidozincates prepared from
exo
-(α
R
)- or
endo
-(α
S
)-
N
-(α-phenylethyl)bornylamine (
H-
exo
-born-
R
or
H-
endo
-born-
S
) were tested; the best results (27% yield and 62% ee in favor of the
R
P
enantiomer) were obtained by using Bu
2
(
endo
-born-
S
)ZnLi in tetrahydrofuran (THF) at −30 °C before iodolysis. Due to the low compatibility of FcCO
2
Me with alkyl-containing lithium zincates, 1 : 1 mixtures of lithium and zinc amides were tested. Chiral (
H-
exo
-born-
R
or
H-
endo
-born-
S
) or/and achiral (lithium 2,2,6,6-tetramethylpiperidide or lithium diisopropylamide) secondary amines gave good results, the best (81% yield and 44% ee in favor of the
R
P
enantiomer) being obtained by using (
endo
-born-
S
)
3
ZnLi in THF at room temperature. Among other secondary amines also prepared and/or tested, commercial (
S
,
S
)-bis(α-phenylethyl)amine (
H-PEA-
S
) proved promising. After optimization of the reaction conditions, the best enantioselectivity (26% yield and 80% ee in favor of the
R
P
enantiomer) was observed by treating a THF solution of FcCO
2
Me and Zn(PEA-
S
)
2
with Li-PEA-
S
at −80 °C before iodolysis. That no reaction took place with cadmium instead of zinc suggests the formation of 'ate complexes upon treatment of Cd(PEA-
S
)
2
by Li-PEA-
S
while Zn(PEA-
S
)
2
and Li-PEA-
S
would rather work in tandem (Li-PEA-
S
as the base and Zn(PEA-
S
)
2
as the
in situ
trap for the formed ferrocenyllithium). While FcCO
2
Me, FcCO
2
t
Bu and FcCO
2
iPr could be converted into their racemic 2-iodinated derivatives with a yield of 84 to 87% by employing LiTMP (2 equiv.) in the presence of ZnCl
2
·TMEDA (1 equiv.) as an
in situ
trap, their enantioselective deprotometalation rather required Li-PEA-
S
together with Zn(PEA-
S
)
2
to produce the enantio-enriched derivatives with yields of 45-82% and 71% ee.
Our attempts to deprotometalate alkyl ferrocenecarboxylates enantioselectively by using chiral lithium-zinc or lithium-cadmium bases are reported.</abstract><cop>Cambridge</cop><pub>Royal Society of Chemistry</pub><doi>10.1039/d1nj04526a</doi><tpages>12</tpages><orcidid>https://orcid.org/0000-0003-3693-8861</orcidid><orcidid>https://orcid.org/0000-0002-2906-2091</orcidid><orcidid>https://orcid.org/0000-0003-4905-1581</orcidid><orcidid>https://orcid.org/0000-0001-9423-995X</orcidid><orcidid>https://orcid.org/0000-0002-7482-9351</orcidid><orcidid>https://orcid.org/0000-0002-6088-4472</orcidid><orcidid>https://orcid.org/0000-0002-4982-6589</orcidid><oa>free_for_read</oa></addata></record> |
| fulltext | fulltext |
| identifier | ISSN: 1144-0546 |
| ispartof | New journal of chemistry, 2021-12, Vol.45 (48), p.22579-2259 |
| issn | 1144-0546 1369-9261 |
| language | eng |
| recordid | cdi_hal_primary_oai_HAL_hal_03464801v1 |
| source | Royal Society Of Chemistry Journals 2008-; Alma/SFX Local Collection |
| subjects | Amides Amines Bimetals Cadmium catalytic synthesis Chemical Sciences Chemistry chemoselective base diastereoselective deprotonative metalation directed ortho-metalation Enantiomers esters ferrocenes Kemi Lithium mediated asymmetric-synthesis mixed lithium-cadmium Optimization ortho-lithiation planar chiral Room temperature Substrates Tetrahydrofuran tmp-zincate Zinc chloride Zincates |
| title | Enantioselective deprotometalation of alkyl ferrocenecarboxylates using bimetallic bases |
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