Reaction Rate Acceleration Enabled by Tethered Lewis Acid-Lewis Base Bifunctional Catalysis: A Catalytic, Enantioselective [2+2] Ketene Aldehyde Cycloaddition Reaction

被引：13

作者：

Chidara, Sridhar ^{[1
]}

Lin, Yun-Ming ^{[1
]}

机构：

[1] Univ Toledo, Dept Chem, Toledo, OH 43606 USA

来源：

SYNLETT | 2009年 / 10期

关键词：

Lewis acids; Lewis bases; bifunctional catalysts; rate acceleration; enantioselectivity; BETA-LACTONES; ASYMMETRIC-SYNTHESIS; DISUBSTITUTED KETENES; COMPLEXES; CHEMISTRY; ORGANOCATALYSIS; 2-OXETANONES; MECHANISM; SYSTEMS; LIGAND;

D O I：

10.1055/s-0029-1217332

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A tethered Lewis acid-Lewis base (LA*-LB*) bifunctional catalyst promotes the asymmetric [2+2] cycloaddition reaction between ketene and aldehydes rapidly. The LA*-LB* bifunctional catalyst, a quinine tethered Co(III)-salen complex (5 mol%) catalyzes the [2+2] cycloaddition reaction to produce the C4-substituted beta-lactones in uniformly >99% ee and high isolated yields (71-97%). The dramatic rate acceleration, the hallmark of cooperative intramolecular bifunctional catalysis, is achieved for the catalytic, enantioselective [2+2] cycloaddition reaction between aldehydes and unsubstituted ketene.

引用

页码：1675 / 1679

页数：5

共 44 条

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