Asymmetric Allylic Alkylation of Alkanoic‐Acid Ester Enolates
A protocol for the direct palladium‐catalyzed asymmetric allylic alkylation of simple alkanoic‐acid esters through their lithium enolates has been developed. The method permits to create stereogenic centers in the homo‐allylic or allylic position. The configuration of the allylation products has bee...
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| Veröffentlicht in: | European journal of organic chemistry 2019-07, Vol.2019 (28), p.4604-4608 |
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| container_issue | 28 |
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| container_title | European journal of organic chemistry |
| container_volume | 2019 |
| creator | Visse, Robin Möllemann, Martin‐Alexander Braun, Manfred |
| description | A protocol for the direct palladium‐catalyzed asymmetric allylic alkylation of simple alkanoic‐acid esters through their lithium enolates has been developed. The method permits to create stereogenic centers in the homo‐allylic or allylic position. The configuration of the allylation products has been elucidated.
The palladium‐catalyzed enantioselective allylic alkylation of nonstabilized lithium enolates is a long‐standing problem in asymmetric syntheses. A protocol based upon suitable reaction conditions and appropriate ligands enables the asymmetric allylation of alkanoic‐acid esters through their lithium enolates in a direct manner that does not require detours via ester surrogates. Thus, stereogenic centers can be created either in allylic or homo‐allylic position. |
| doi_str_mv | 10.1002/ejoc.201900822 |
| format | Article |
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The palladium‐catalyzed enantioselective allylic alkylation of nonstabilized lithium enolates is a long‐standing problem in asymmetric syntheses. A protocol based upon suitable reaction conditions and appropriate ligands enables the asymmetric allylation of alkanoic‐acid esters through their lithium enolates in a direct manner that does not require detours via ester surrogates. Thus, stereogenic centers can be created either in allylic or homo‐allylic position.</description><identifier>ISSN: 1434-193X</identifier><identifier>EISSN: 1099-0690</identifier><identifier>DOI: 10.1002/ejoc.201900822</identifier><language>eng</language><publisher>Weinheim: Wiley Subscription Services, Inc</publisher><subject>Alkylation ; Allyl compounds ; Catalysis ; Chemical reactions ; Enantioselectivity ; Esters ; Lithium ; Palladium ; Synthetic methods</subject><ispartof>European journal of organic chemistry, 2019-07, Vol.2019 (28), p.4604-4608</ispartof><rights>2019 WILEY‐VCH Verlag GmbH & Co. KGaA, Weinheim</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c3172-6d6dad18fc0e27253d030ab2e70fa09e6526733c5ed916e3c1242ef1fab6351e3</citedby><cites>FETCH-LOGICAL-c3172-6d6dad18fc0e27253d030ab2e70fa09e6526733c5ed916e3c1242ef1fab6351e3</cites><orcidid>0000-0002-7614-8090</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.201900822$$EPDF$$P50$$Gwiley$$H</linktopdf><linktohtml>$$Uhttps://onlinelibrary.wiley.com/doi/full/10.1002%2Fejoc.201900822$$EHTML$$P50$$Gwiley$$H</linktohtml><link.rule.ids>314,776,780,1411,27901,27902,45550,45551</link.rule.ids></links><search><creatorcontrib>Visse, Robin</creatorcontrib><creatorcontrib>Möllemann, Martin‐Alexander</creatorcontrib><creatorcontrib>Braun, Manfred</creatorcontrib><title>Asymmetric Allylic Alkylation of Alkanoic‐Acid Ester Enolates</title><title>European journal of organic chemistry</title><description>A protocol for the direct palladium‐catalyzed asymmetric allylic alkylation of simple alkanoic‐acid esters through their lithium enolates has been developed. The method permits to create stereogenic centers in the homo‐allylic or allylic position. The configuration of the allylation products has been elucidated.
The palladium‐catalyzed enantioselective allylic alkylation of nonstabilized lithium enolates is a long‐standing problem in asymmetric syntheses. A protocol based upon suitable reaction conditions and appropriate ligands enables the asymmetric allylation of alkanoic‐acid esters through their lithium enolates in a direct manner that does not require detours via ester surrogates. Thus, stereogenic centers can be created either in allylic or homo‐allylic position.</description><subject>Alkylation</subject><subject>Allyl compounds</subject><subject>Catalysis</subject><subject>Chemical reactions</subject><subject>Enantioselectivity</subject><subject>Esters</subject><subject>Lithium</subject><subject>Palladium</subject><subject>Synthetic methods</subject><issn>1434-193X</issn><issn>1099-0690</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2019</creationdate><recordtype>article</recordtype><recordid>eNqFkE1Lw0AQhhdRsFavngOeU2dnm033JKHELwq9KHhbtptZSE2zdTciufkT_I3-ElMrevT0zsDzzsDD2DmHCQfAS1p7O0HgCmCGeMBGHJRKQSo4HOapmKZciadjdhLjGgCUlHzErorYbzbUhdomRdP0zXc-943pat8m3u020_rafr5_FLaukjJ2FJKy9QNC8ZQdOdNEOvvJMXu8Lh_mt-lieXM3LxapFTzHVFayMhWfOQuEOWaiAgFmhZSDM6BIZihzIWxGleKShOU4RXLcmZUUGScxZhf7u9vgX14pdnrtX0M7vNSIUmIms5kYqMmessHHGMjpbag3JvSag95J0jtJ-lfSUFD7wlvdUP8Prcv75fyv-wWeCGto</recordid><startdate>20190731</startdate><enddate>20190731</enddate><creator>Visse, Robin</creator><creator>Möllemann, Martin‐Alexander</creator><creator>Braun, Manfred</creator><general>Wiley Subscription Services, Inc</general><scope>AAYXX</scope><scope>CITATION</scope><orcidid>https://orcid.org/0000-0002-7614-8090</orcidid></search><sort><creationdate>20190731</creationdate><title>Asymmetric Allylic Alkylation of Alkanoic‐Acid Ester Enolates</title><author>Visse, Robin ; Möllemann, Martin‐Alexander ; Braun, Manfred</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c3172-6d6dad18fc0e27253d030ab2e70fa09e6526733c5ed916e3c1242ef1fab6351e3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2019</creationdate><topic>Alkylation</topic><topic>Allyl compounds</topic><topic>Catalysis</topic><topic>Chemical reactions</topic><topic>Enantioselectivity</topic><topic>Esters</topic><topic>Lithium</topic><topic>Palladium</topic><topic>Synthetic methods</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Visse, Robin</creatorcontrib><creatorcontrib>Möllemann, Martin‐Alexander</creatorcontrib><creatorcontrib>Braun, Manfred</creatorcontrib><collection>CrossRef</collection><jtitle>European journal of organic chemistry</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Visse, Robin</au><au>Möllemann, Martin‐Alexander</au><au>Braun, Manfred</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Asymmetric Allylic Alkylation of Alkanoic‐Acid Ester Enolates</atitle><jtitle>European journal of organic chemistry</jtitle><date>2019-07-31</date><risdate>2019</risdate><volume>2019</volume><issue>28</issue><spage>4604</spage><epage>4608</epage><pages>4604-4608</pages><issn>1434-193X</issn><eissn>1099-0690</eissn><abstract>A protocol for the direct palladium‐catalyzed asymmetric allylic alkylation of simple alkanoic‐acid esters through their lithium enolates has been developed. The method permits to create stereogenic centers in the homo‐allylic or allylic position. The configuration of the allylation products has been elucidated.
The palladium‐catalyzed enantioselective allylic alkylation of nonstabilized lithium enolates is a long‐standing problem in asymmetric syntheses. A protocol based upon suitable reaction conditions and appropriate ligands enables the asymmetric allylation of alkanoic‐acid esters through their lithium enolates in a direct manner that does not require detours via ester surrogates. Thus, stereogenic centers can be created either in allylic or homo‐allylic position.</abstract><cop>Weinheim</cop><pub>Wiley Subscription Services, Inc</pub><doi>10.1002/ejoc.201900822</doi><tpages>5</tpages><orcidid>https://orcid.org/0000-0002-7614-8090</orcidid></addata></record> |
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| ispartof | European journal of organic chemistry, 2019-07, Vol.2019 (28), p.4604-4608 |
| issn | 1434-193X 1099-0690 |
| language | eng |
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| source | Wiley Online Library Journals Frontfile Complete |
| subjects | Alkylation Allyl compounds Catalysis Chemical reactions Enantioselectivity Esters Lithium Palladium Synthetic methods |
| title | Asymmetric Allylic Alkylation of Alkanoic‐Acid Ester Enolates |
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