Studies on the Bisoxazoline‐ and (−)‐Sparteine‐Mediated Enantioselective Addition of Organolithium Reagents to Imines
Identifieur interne : 000507 ( Main/Exploration ); précédent : 000506; suivant : 000508Studies on the Bisoxazoline‐ and (−)‐Sparteine‐Mediated Enantioselective Addition of Organolithium Reagents to Imines
Auteurs : Scott Denmark [États-Unis] ; Noriyuki Nakajima ; Cory Stiff ; Olivier J. Nicaise ; Michael KranzSource :
- Advanced Synthesis & Catalysis [ 1615-4150 ] ; 2008-05-05.
English descriptors
Abstract
The enantioselective addition of organolithium reagents to N‐anisylaldimines promoted by chiral bisoxazolines and (−)‐sparteine as external ligands is described. This reaction proceeds readily with a wide range of aldimine substrates (aliphatic, aromatic, olefinic) and organolithium nucleophiles (Me, n‐Bu, Ph, vinyl) in excellent yields (81–99%) and with high enantioselectivities (up to 97:3.0 er). The external ligands can be used in substoichiometric amounts albeit with slightly attenuated enantioselectivities. A systematic evaluation of the structural features of the bisoxazolines revealed a primary contribution from the substituent at C(4) and a secondary influence from the bridging substituents. A computational analysis (PM3) provided a clear rationalization for the origin of enantioselectivity.
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DOI: 10.1002/adsc.200800017
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Catal.</title><idno type="ISSN">1615-4150</idno><idno type="eISSN">1615-4169</idno><imprint><publisher>WILEY‐VCH Verlag</publisher><pubPlace>Weinheim</pubPlace><date type="published" when="2008-05-05">2008-05-05</date><biblScope unit="volume">350</biblScope><biblScope unit="issue">7‐8</biblScope><biblScope unit="page" from="1023">1023</biblScope><biblScope unit="page" to="1045">1045</biblScope></imprint><idno type="ISSN">1615-4150</idno></series><idno type="istex">865A9C46370ECF9FE798F6DA78821BBD04F95BD1</idno><idno type="DOI">10.1002/adsc.200800017</idno><idno type="ArticleID">ADSC200800017</idno></biblStruct></sourceDesc><seriesStmt><idno type="ISSN">1615-4150</idno></seriesStmt></fileDesc><profileDesc><textClass><keywords scheme="KwdEn" xml:lang="en"><term>aldimines</term><term>bisoxazolines</term><term>catalysis</term><term>enantioselective addition</term><term>organolithium reagents</term></keywords></textClass><langUsage><language ident="en">en</language></langUsage></profileDesc></teiHeader><front><div type="abstract" xml:lang="en">The enantioselective addition of organolithium reagents to N‐anisylaldimines promoted by chiral bisoxazolines and (−)‐sparteine as external ligands is described. This reaction proceeds readily with a wide range of aldimine substrates (aliphatic, aromatic, olefinic) and organolithium nucleophiles (Me, n‐Bu, Ph, vinyl) in excellent yields (81–99%) and with high enantioselectivities (up to 97:3.0 er). The external ligands can be used in substoichiometric amounts albeit with slightly attenuated enantioselectivities. A systematic evaluation of the structural features of the bisoxazolines revealed a primary contribution from the substituent at C(4) and a secondary influence from the bridging substituents. 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