Catalytic asymmetric propionate aldol reactions via acyl halide-aldehyde cyclocondensations

被引：53

作者：

Nelson, SG ^{[1
]}

Wan, ZH ^{[1
]}

机构：

[1] Univ Pittsburgh, Dept Chem, Pittsburgh, PA 15260 USA

来源：

ORGANIC LETTERS | 2000年 / 2卷 / 13期

关键词：

D O I：

10.1021/ol005968e

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Catalyzed asymmetric acyl halide-aldehyde cyclocondensation (AAC) reactions afford highly enantiomerically enriched 3,4-disubstituted-2-oxetanones. These reactions constitute catalytic asymmetric propionate aldol additions. An optically active Al(III)-triamine complex (10 mol %) catalyzes the di(isopropyl)ethylamine-mediated cyclocondensation of propionyl bromide and a variety of aldehydes to afford beta-lactone adducts with uniformly high enantioselection (90 --> 98% ee), diastereoselection (74 --> 98% de), and chemical yields (78-90%). Lactone ring opening reveals that the enantiomerically enriched beta-lactones act as surrogates for syn propionate aldol adducts.

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页码：1883 / 1886

页数：4

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