Asymmetric Synthesis of 1,3-Dioxolanes by Organocatalytic Formal [3+2] Cycloaddition via Hemiacetal Intermediates

被引：74

作者：

Asano, Keisuke ^{[1
]}

Matsubara, Seijiro ^{[1
]}

机构：

[1] Kyoto Univ, Grad Sch Engn, Dept Chem Mat, Nishikyo Ku, Kyoto 6158510, Japan

来源：

ORGANIC LETTERS | 2012年 / 14卷 / 06期

基金：

日本学术振兴会;

关键词：

DOUBLE-BOND ISOMERIZATION; OXY-MICHAEL ADDITION; CHIRAL ACETALS; CONJUGATE ADDITION; ACID; RESOLUTION; TEMPLATES; ALPHA; CYCLIZATION; INDUCTION;

D O I：

10.1021/ol3003755

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A novel asymmetric formal [3 + 2] cycloaddition reaction for the synthesis of 1,3-dioxolanes using cinchona-alkaloid-thiourea-based bifunctional organocatalysts is reported. The reaction proceeds via the formation of hemiacetal intermediates between gamma-hydroxy-alpha,beta-unsaturated ketones and aldehydes.

引用

页码：1620 / 1623

页数：4

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