Asymmetric Homoenolate Additions to Acyl Phosphonates through Rational Design of a Tailored N-Heterocyclic Carbene Catalyst

被引：77

作者：

Jang, Ki Po ^{[1
]}

Hutson, Gerri E. ^{[1
]}

Johnston, Ryne C. ^{[2
]}

McCusker, Elizabeth O. ^{[1
]}

Cheong, Paul H-Y ^{[2
]}

Scheidt, Karl A. ^{[1
]}

机构：

[1] Northwestern Univ, Ctr Mol Innovat & Drug Discovery, Chem Life Proc Inst, Dept Chem, Evanston, IL 60208 USA

[2] Oregon State Univ, Dept Chem, Corvallis, OR 97331 USA

来源：

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 2014年 / 136卷 / 01期

关键词：

INTERMOLECULAR STETTER REACTION; STEREOSELECTIVE-SYNTHESIS; ENANTIOSELECTIVE SYNTHESIS; ALPHA; BETA-UNSATURATED ALDEHYDES; COOPERATIVE CATALYSIS; GAMMA-BUTYROLACTONES; CONJUGATE UMPOLUNG; DIRECT ANNULATIONS; ENALS; CHALCONES;

D O I：

10.1021/ja410932t

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

A highly selective NHC-catalyzed synthesis of gamma-butyrolactones from the fusion of enals and alpha-ketophosphonates has been developed. Computational modeling of competing transition states guided a rational design strategy to achieve enhanced levels of enantioselectivity with a new tailored C-1-symmetric biaryl-saturated imidazolium-derived NHC catalyst.

引用

页码：76 / 79

页数：4

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