N-Heterocyclic Carbene-Mediated Enantioselective Addition of Phenols to Unsymmetrical Alkylarylketenes

被引：72

作者：

Concellon, Carmen ^{[1
]}

Duguet, Nicolas ^{[1
]}

Smith, Andrew D. ^{[1
]}

机构：

[1] Univ St Andrews, Sch Chem, EaStCHEM, St Andrews KY16 9ST, Fife, Scotland

来源：

ADVANCED SYNTHESIS & CATALYSIS | 2009年 / 351卷 / 17期

基金：

英国工程与自然科学研究理事会;

关键词：

asymmetric catalysis; enantioselectivity; esters; ketenes; N-heterocyclic carbenes; organocatalysis; INTERMOLECULAR STETTER REACTION; DIELS-ALDER REACTIONS; CATALYZED RING EXPANSION; SYNTHESEN MIT KETENEN; C-CARBOXYL TRANSFER; ASYMMETRIC-SYNTHESIS; ALPHA; BETA-UNSATURATED ALDEHYDES; SECONDARY ALCOHOLS; ZWITTERIONIC POLYMERIZATION; STEREOSELECTIVE-SYNTHESIS;

D O I：

10.1002/adsc.200900538

中图分类号：

O69 [应用化学];

学科分类号：

081704 ;

摘要：

Chiral N-heterocyclic carbenes (NHCs) mediate the enantioselective addition of 2-phenylphenol to unsymmetrical alkylarylketenes, delivering alpha-alkyl-alpha-arylacetic acid derivatives with good levels of enantiocontrol (up to 84% ee). Enantiodivergent stereochemical outcomes are observed using 2-phenylphenol and benzhydrol in the NHC-promoted esterification reaction using a triazolium precatalyst derived from pyroglutamic acid, consistent with distinct mechanistic pathways operating within these processes.

引用

页码：3001 / 3009

页数：9

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