Synthesis of Enantioenriched α,α-Disubstituted Cyclopentenes Catalyzed by N-Heterocyclic Carbenes

被引：16

作者：

Phillips, Eric M. ^{[1
]}

Wadamoto, Manabu ^{[1
]}

Scheidt, Karl A. ^{[1
]}

机构：

[1] Northwestern Univ, Dept Chem, Evanston, IL 60208 USA

来源：

SYNTHESIS-STUTTGART | 2009年 / 04期

关键词：

carbenes; asymmetric catalysis; Umpolung; beta-lactones; aldol reactions; CARBON QUATERNARY STEREOCENTERS; ENANTIOSELECTIVE CONSTRUCTION; NUCLEOPHILIC CARBENES; ASYMMETRIC-SYNTHESIS; ORGANIC-SYNTHESIS; ESTERS; HOMOENOLATE; ALDEHYDES; KETONES;

D O I：

10.1055/s-0028-1083284

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The desymmetrization of 1,3-diketones using N-heterocyclic carbenes results in the formation of highly enantioenriched cyclopentenes in good yield. The reaction proceeds through a catalytic intramolecular aldol reaction and subsequent beta-lactone formation. The expulsion of carbon dioxide at mild reaction temperatures affords the cyclopentene products.

引用

页码：687 / 690

页数：4

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