Chiral Phosphinoferrocenyl-Calixarenes
The Mitsunobu alkylation of 4‐tert‐butylcalix[4]arene with (S)‐(2‐diphenylthiophosphinoferrocenyl)methanol followed by desulfuration of the thiophosphine unit using tris(dimethylamino)phosphine afforded enantiomerically pure calixarene mono‐ and di(ferrocenylphosphine) ligands in high yields. The ca...
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| Veröffentlicht in: | European journal of organic chemistry 2016-07, Vol.2016 (20), p.3386-3394 |
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| container_title | European journal of organic chemistry |
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| creator | Karpus, Andrii Yesypenko, Oleksandr Boiko, Vyacheslav Poli, Rinaldo Daran, Jean-Claude Voitenko, Zoia Kalchenko, Vitaly Manoury, Eric |
| description | The Mitsunobu alkylation of 4‐tert‐butylcalix[4]arene with (S)‐(2‐diphenylthiophosphinoferrocenyl)methanol followed by desulfuration of the thiophosphine unit using tris(dimethylamino)phosphine afforded enantiomerically pure calixarene mono‐ and di(ferrocenylphosphine) ligands in high yields. The calixarene mono(ferrocenylphosphine) ligands exhibited good catalytic activity but low atropoenantioselectivity when used in the asymmetric Suzuki–Miyaura coupling reaction of 1‐naphthaleneboronic acid and 1‐bromo‐2‐methylnaphthalene. However, the di(ferrocenylphosphine) ligand displayed both good catalytic activity and enantioselectivity (ee values up to 86 %) when employed in the asymmetric Tsuji–Trost allylic alkylation of 1,3‐diphenylprop‐2‐enyl acetate with dimethyl malonate.
The Mitsunobu alkylation of 4‐tert‐butylcalix[4]arene and (S)‐(2‐diphenylthiophosphinoferrocenyl)methanol followed by desulfuration gave enantiomerically pure calixarene mono‐ and di(ferrocenylphosphine) ligands. These ligands have good catalytic activity, but the di(ferrocenylphosphine) ligand also showed good enantioselectivity (up to 86 % ee) in an asymmetric Tsuji–Trost allylic alkylation. |
| doi_str_mv | 10.1002/ejoc.201600208 |
| format | Article |
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The Mitsunobu alkylation of 4‐tert‐butylcalix[4]arene and (S)‐(2‐diphenylthiophosphinoferrocenyl)methanol followed by desulfuration gave enantiomerically pure calixarene mono‐ and di(ferrocenylphosphine) ligands. These ligands have good catalytic activity, but the di(ferrocenylphosphine) ligand also showed good enantioselectivity (up to 86 % ee) in an asymmetric Tsuji–Trost allylic alkylation.</description><identifier>ISSN: 1434-193X</identifier><identifier>EISSN: 1099-0690</identifier><identifier>DOI: 10.1002/ejoc.201600208</identifier><language>eng</language><publisher>Weinheim: Blackwell Publishing Ltd</publisher><subject>Alkylation ; Asymmetric catalysis ; Calixarenes ; Chemical Sciences ; Coordination chemistry ; Cyclopentadienyl ligands ; Ligands ; Phosphorus</subject><ispartof>European journal of organic chemistry, 2016-07, Vol.2016 (20), p.3386-3394</ispartof><rights>2016 WILEY‐VCH Verlag GmbH & Co. KGaA, Weinheim</rights><rights>2016 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim</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-c4298-3b4bbc8716ff5786813431690ced497655d557682fdeb0fbf909ff90967847fd3</citedby><cites>FETCH-LOGICAL-c4298-3b4bbc8716ff5786813431690ced497655d557682fdeb0fbf909ff90967847fd3</cites><orcidid>0000-0001-7991-8890 ; 0000-0002-5220-2515 ; 0000-0002-5760-3086</orcidid></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktopdf>$$Uhttps://onlinelibrary.wiley.com/doi/pdf/10.1002%2Fejoc.201600208$$EPDF$$P50$$Gwiley$$H</linktopdf><linktohtml>$$Uhttps://onlinelibrary.wiley.com/doi/full/10.1002%2Fejoc.201600208$$EHTML$$P50$$Gwiley$$H</linktohtml><link.rule.ids>230,314,778,782,883,1414,27911,27912,45561,45562</link.rule.ids><backlink>$$Uhttps://hal.science/hal-01929761$$DView record in HAL$$Hfree_for_read</backlink></links><search><creatorcontrib>Karpus, Andrii</creatorcontrib><creatorcontrib>Yesypenko, Oleksandr</creatorcontrib><creatorcontrib>Boiko, Vyacheslav</creatorcontrib><creatorcontrib>Poli, Rinaldo</creatorcontrib><creatorcontrib>Daran, Jean-Claude</creatorcontrib><creatorcontrib>Voitenko, Zoia</creatorcontrib><creatorcontrib>Kalchenko, Vitaly</creatorcontrib><creatorcontrib>Manoury, Eric</creatorcontrib><title>Chiral Phosphinoferrocenyl-Calixarenes</title><title>European journal of organic chemistry</title><addtitle>Eur. J. Org. Chem</addtitle><description>The Mitsunobu alkylation of 4‐tert‐butylcalix[4]arene with (S)‐(2‐diphenylthiophosphinoferrocenyl)methanol followed by desulfuration of the thiophosphine unit using tris(dimethylamino)phosphine afforded enantiomerically pure calixarene mono‐ and di(ferrocenylphosphine) ligands in high yields. The calixarene mono(ferrocenylphosphine) ligands exhibited good catalytic activity but low atropoenantioselectivity when used in the asymmetric Suzuki–Miyaura coupling reaction of 1‐naphthaleneboronic acid and 1‐bromo‐2‐methylnaphthalene. However, the di(ferrocenylphosphine) ligand displayed both good catalytic activity and enantioselectivity (ee values up to 86 %) when employed in the asymmetric Tsuji–Trost allylic alkylation of 1,3‐diphenylprop‐2‐enyl acetate with dimethyl malonate.
The Mitsunobu alkylation of 4‐tert‐butylcalix[4]arene and (S)‐(2‐diphenylthiophosphinoferrocenyl)methanol followed by desulfuration gave enantiomerically pure calixarene mono‐ and di(ferrocenylphosphine) ligands. These ligands have good catalytic activity, but the di(ferrocenylphosphine) ligand also showed good enantioselectivity (up to 86 % ee) in an asymmetric Tsuji–Trost allylic alkylation.</description><subject>Alkylation</subject><subject>Asymmetric catalysis</subject><subject>Calixarenes</subject><subject>Chemical Sciences</subject><subject>Coordination chemistry</subject><subject>Cyclopentadienyl ligands</subject><subject>Ligands</subject><subject>Phosphorus</subject><issn>1434-193X</issn><issn>1099-0690</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2016</creationdate><recordtype>article</recordtype><recordid>eNqFkM1LwzAYh4MoOKdXz4IgeOh807T5OI4yN2VM8QN3C2mb0M66zGTT7b83pTK8eckXz_PjzQ-hcwwDDBDf6IUtBjFgGi7AD1APgxARUAGH4ZyQJMKCzI_RifcLABCU4h66yqraqebisbJ-VdVLa7RzttDLXRNlqqm3yuml9qfoyKjG67PfvY9eb0cv2SSaPozvsuE0KpJY8IjkSZ4XnGFqTMo45ZgkBIcJCl0mgtE0LdOUUR6bUudgciNAmHahjCfMlKSPrrvcSjVy5eoP5XbSqlpOhlPZvgEWcQjCXziwlx27cvZzo_1aLuzGLcN4EnNIePgtjQM16KjCWe-dNvtYDLLtTba9yX1vQRCd8F03evcPLUf3D9lfN-rc2q_1du8q9y4pIyyVb7OxzCbx0_w5nUlOfgCBT34w</recordid><startdate>201607</startdate><enddate>201607</enddate><creator>Karpus, Andrii</creator><creator>Yesypenko, Oleksandr</creator><creator>Boiko, Vyacheslav</creator><creator>Poli, Rinaldo</creator><creator>Daran, Jean-Claude</creator><creator>Voitenko, Zoia</creator><creator>Kalchenko, Vitaly</creator><creator>Manoury, Eric</creator><general>Blackwell Publishing Ltd</general><general>Wiley Subscription Services, Inc</general><general>Wiley-VCH Verlag</general><scope>BSCLL</scope><scope>AAYXX</scope><scope>CITATION</scope><scope>1XC</scope><scope>VOOES</scope><orcidid>https://orcid.org/0000-0001-7991-8890</orcidid><orcidid>https://orcid.org/0000-0002-5220-2515</orcidid><orcidid>https://orcid.org/0000-0002-5760-3086</orcidid></search><sort><creationdate>201607</creationdate><title>Chiral Phosphinoferrocenyl-Calixarenes</title><author>Karpus, Andrii ; Yesypenko, Oleksandr ; Boiko, Vyacheslav ; Poli, Rinaldo ; Daran, Jean-Claude ; Voitenko, Zoia ; Kalchenko, Vitaly ; Manoury, Eric</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c4298-3b4bbc8716ff5786813431690ced497655d557682fdeb0fbf909ff90967847fd3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2016</creationdate><topic>Alkylation</topic><topic>Asymmetric catalysis</topic><topic>Calixarenes</topic><topic>Chemical Sciences</topic><topic>Coordination chemistry</topic><topic>Cyclopentadienyl ligands</topic><topic>Ligands</topic><topic>Phosphorus</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Karpus, Andrii</creatorcontrib><creatorcontrib>Yesypenko, Oleksandr</creatorcontrib><creatorcontrib>Boiko, Vyacheslav</creatorcontrib><creatorcontrib>Poli, Rinaldo</creatorcontrib><creatorcontrib>Daran, Jean-Claude</creatorcontrib><creatorcontrib>Voitenko, Zoia</creatorcontrib><creatorcontrib>Kalchenko, Vitaly</creatorcontrib><creatorcontrib>Manoury, Eric</creatorcontrib><collection>Istex</collection><collection>CrossRef</collection><collection>Hyper Article en Ligne (HAL)</collection><collection>Hyper Article en Ligne (HAL) (Open Access)</collection><jtitle>European journal of organic chemistry</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Karpus, Andrii</au><au>Yesypenko, Oleksandr</au><au>Boiko, Vyacheslav</au><au>Poli, Rinaldo</au><au>Daran, Jean-Claude</au><au>Voitenko, Zoia</au><au>Kalchenko, Vitaly</au><au>Manoury, Eric</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Chiral Phosphinoferrocenyl-Calixarenes</atitle><jtitle>European journal of organic chemistry</jtitle><addtitle>Eur. J. Org. Chem</addtitle><date>2016-07</date><risdate>2016</risdate><volume>2016</volume><issue>20</issue><spage>3386</spage><epage>3394</epage><pages>3386-3394</pages><issn>1434-193X</issn><eissn>1099-0690</eissn><abstract>The Mitsunobu alkylation of 4‐tert‐butylcalix[4]arene with (S)‐(2‐diphenylthiophosphinoferrocenyl)methanol followed by desulfuration of the thiophosphine unit using tris(dimethylamino)phosphine afforded enantiomerically pure calixarene mono‐ and di(ferrocenylphosphine) ligands in high yields. The calixarene mono(ferrocenylphosphine) ligands exhibited good catalytic activity but low atropoenantioselectivity when used in the asymmetric Suzuki–Miyaura coupling reaction of 1‐naphthaleneboronic acid and 1‐bromo‐2‐methylnaphthalene. However, the di(ferrocenylphosphine) ligand displayed both good catalytic activity and enantioselectivity (ee values up to 86 %) when employed in the asymmetric Tsuji–Trost allylic alkylation of 1,3‐diphenylprop‐2‐enyl acetate with dimethyl malonate.
The Mitsunobu alkylation of 4‐tert‐butylcalix[4]arene and (S)‐(2‐diphenylthiophosphinoferrocenyl)methanol followed by desulfuration gave enantiomerically pure calixarene mono‐ and di(ferrocenylphosphine) ligands. These ligands have good catalytic activity, but the di(ferrocenylphosphine) ligand also showed good enantioselectivity (up to 86 % ee) in an asymmetric Tsuji–Trost allylic alkylation.</abstract><cop>Weinheim</cop><pub>Blackwell Publishing Ltd</pub><doi>10.1002/ejoc.201600208</doi><tpages>9</tpages><orcidid>https://orcid.org/0000-0001-7991-8890</orcidid><orcidid>https://orcid.org/0000-0002-5220-2515</orcidid><orcidid>https://orcid.org/0000-0002-5760-3086</orcidid><oa>free_for_read</oa></addata></record> |
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| subjects | Alkylation Asymmetric catalysis Calixarenes Chemical Sciences Coordination chemistry Cyclopentadienyl ligands Ligands Phosphorus |
| title | Chiral Phosphinoferrocenyl-Calixarenes |
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