Cinchona alkaloid-Lewis acid catalyst systems for enantioselective ketene-aldehyde cycloadditions

被引：163

作者：

Zhu, C ^{[1
]}

Shen, XQ ^{[1
]}

Nelson, SG ^{[1
]}

机构：

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

来源：

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 2004年 / 126卷 / 17期

关键词：

D O I：

10.1021/ja0492900

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Asymmetric cinchona alkaloid-catalyzed acid chloride-aldehyde cyclocondensation (AAC) reactions afford enantioenriched 4-substituted and 3,4-disubstituted β-lactones with near perfect absolute and relative stereocontrol. These reactions are characterized by the operational simplicity derived from using commercially available or easily obtained (one-step) reaction catalysts and in situ ketene generation from acid chlorides. The range of aldehyde substrates that serve as effective AAC substrates include sterically hindered aldehydes such as cyclohexanecarboxaldehyde and pivaldehyde. Copyright © 2003 American Chemical Society.

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页码：5352 / 5353

页数：2

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