Cumyl Ester as the C-Terminal Protecting Group in the Enantioselective Alkylation of Glycine Benzophenone Imine

Cumyl ester is an optimal C-terminal protecting group for glycine benzophenone imine in asymmetric alkylation reactions catalyzed by Cinchona chiral phase-transfer catalysts. High levels of enantioselectivity have been obtained (up to 94% ee) with this substrate, which provides an attractive alterna...

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Veröffentlicht in:	Organic letters 2012-01, Vol.14 (1), p.150-153
Hauptverfasser:	Respondek, Tomasz, Cueny, Eric, Kodanko, Jeremy J
Format:	Artikel
Sprache:	eng
Schlagworte:	Alkylation Benzophenones - chemistry Esters Glycine - analogs & derivatives Glycine - chemistry Imines - chemistry Molecular Structure Stereoisomerism
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description	Cumyl ester is an optimal C-terminal protecting group for glycine benzophenone imine in asymmetric alkylation reactions catalyzed by Cinchona chiral phase-transfer catalysts. High levels of enantioselectivity have been obtained (up to 94% ee) with this substrate, which provides an attractive alternative to the analogous tert-butyl ester. N-terminal imines and the C-terminal esters can be cleaved from alkylation products by hydrogenolysis, while maintaining acid-labile side chain protecting groups.
doi_str_mv	10.1021/ol202939g
format	Article
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N-terminal imines and the C-terminal esters can be cleaved from alkylation products by hydrogenolysis, while maintaining acid-labile side chain protecting groups.</description><identifier>ISSN: 1523-7060</identifier><identifier>EISSN: 1523-7052</identifier><identifier>DOI: 10.1021/ol202939g</identifier><identifier>PMID: 22149572</identifier><language>eng</language><publisher>United States: American Chemical Society</publisher><subject>Alkylation ; Benzophenones - chemistry ; Esters ; Glycine - analogs & derivatives ; Glycine - chemistry ; Imines - chemistry ; Molecular Structure ; Stereoisomerism</subject><ispartof>Organic letters, 2012-01, Vol.14 (1), p.150-153</ispartof><rights>Copyright © 2011 American Chemical Society</rights><rights>2011 American Chemical Society</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-a380t-afb91cc9283dba56f0152bc1e5c97b7c235e8f93657eb48c0deb9918fba399743</citedby><cites>FETCH-LOGICAL-a380t-afb91cc9283dba56f0152bc1e5c97b7c235e8f93657eb48c0deb9918fba399743</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktopdf>$$Uhttps://pubs.acs.org/doi/pdf/10.1021/ol202939g$$EPDF$$P50$$Gacs$$H</linktopdf><linktohtml>$$Uhttps://pubs.acs.org/doi/10.1021/ol202939g$$EHTML$$P50$$Gacs$$H</linktohtml><link.rule.ids>314,778,782,2754,27063,27911,27912,56725,56775</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/22149572$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Respondek, Tomasz</creatorcontrib><creatorcontrib>Cueny, Eric</creatorcontrib><creatorcontrib>Kodanko, Jeremy J</creatorcontrib><title>Cumyl Ester as the C-Terminal Protecting Group in the Enantioselective Alkylation of Glycine Benzophenone Imine</title><title>Organic letters</title><addtitle>Org. Lett</addtitle><description>Cumyl ester is an optimal C-terminal protecting group for glycine benzophenone imine in asymmetric alkylation reactions catalyzed by Cinchona chiral phase-transfer catalysts. High levels of enantioselectivity have been obtained (up to 94% ee) with this substrate, which provides an attractive alternative to the analogous tert-butyl ester. N-terminal imines and the C-terminal esters can be cleaved from alkylation products by hydrogenolysis, while maintaining acid-labile side chain protecting groups.</description><subject>Alkylation</subject><subject>Benzophenones - chemistry</subject><subject>Esters</subject><subject>Glycine - analogs & derivatives</subject><subject>Glycine - chemistry</subject><subject>Imines - chemistry</subject><subject>Molecular Structure</subject><subject>Stereoisomerism</subject><issn>1523-7060</issn><issn>1523-7052</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2012</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNptkMtOAjEUhhujEUQXvoDpxhgXo73MrUskiCQkusD1pFPOwGCnxXbGBJ_eIsjK1bl9-XLyI3RNyQMljD5azQgTXCxPUJ8mjEcZSdjpsU9JD114vyaEho04Rz3GaCySjPWRHXXNVuOxb8Fh6XG7AjyK5uCa2kiN35xtQbW1WeKJs90G1-YXGRtp2tp60LvrF-Ch_thqGVYG2wpP9FbVBvATmG-7WYGxYZgGJVyis0pqD1eHOkDvz-P56CWavU6mo-EskjwnbSSrUlClBMv5opRJWpHweakoJEpkZaYYTyCvBE-TDMo4V2QBpRA0r0rJhchiPkB3e-_G2c8OfFs0tVegtTRgO18IGqcZySgP5P2eVM5676AqNq5upNsWlBS7eItjvIG9OVi7soHFkfzLMwC3e0AqX6xt50KI_h_RD8nFglU</recordid><startdate>20120106</startdate><enddate>20120106</enddate><creator>Respondek, Tomasz</creator><creator>Cueny, Eric</creator><creator>Kodanko, Jeremy J</creator><general>American Chemical Society</general><scope>CGR</scope><scope>CUY</scope><scope>CVF</scope><scope>ECM</scope><scope>EIF</scope><scope>NPM</scope><scope>AAYXX</scope><scope>CITATION</scope><scope>7X8</scope></search><sort><creationdate>20120106</creationdate><title>Cumyl Ester as the C-Terminal Protecting Group in the Enantioselective Alkylation of Glycine Benzophenone Imine</title><author>Respondek, Tomasz ; Cueny, Eric ; Kodanko, Jeremy J</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-a380t-afb91cc9283dba56f0152bc1e5c97b7c235e8f93657eb48c0deb9918fba399743</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2012</creationdate><topic>Alkylation</topic><topic>Benzophenones - chemistry</topic><topic>Esters</topic><topic>Glycine - analogs & derivatives</topic><topic>Glycine - chemistry</topic><topic>Imines - chemistry</topic><topic>Molecular Structure</topic><topic>Stereoisomerism</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Respondek, Tomasz</creatorcontrib><creatorcontrib>Cueny, Eric</creatorcontrib><creatorcontrib>Kodanko, Jeremy J</creatorcontrib><collection>Medline</collection><collection>MEDLINE</collection><collection>MEDLINE (Ovid)</collection><collection>MEDLINE</collection><collection>MEDLINE</collection><collection>PubMed</collection><collection>CrossRef</collection><collection>MEDLINE - Academic</collection><jtitle>Organic letters</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Respondek, Tomasz</au><au>Cueny, Eric</au><au>Kodanko, Jeremy J</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Cumyl Ester as the C-Terminal Protecting Group in the Enantioselective Alkylation of Glycine Benzophenone Imine</atitle><jtitle>Organic letters</jtitle><addtitle>Org. 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subjects	Alkylation Benzophenones - chemistry Esters Glycine - analogs & derivatives Glycine - chemistry Imines - chemistry Molecular Structure Stereoisomerism
title	Cumyl Ester as the C-Terminal Protecting Group in the Enantioselective Alkylation of Glycine Benzophenone Imine
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