Asymmetric synthesis of bicyclic β-lactones via the intramolecular, nucleophile-catalyzed aldol lactonization:: Improved efficiency and expanded scope

被引：90

作者：

Oh, SH ^{[1
]}

Cortez, GS ^{[1
]}

Romo, D ^{[1
]}

机构：

[1] Texas A&M Univ, Dept Chem, College Stn, TX 77842 USA

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2005年 / 70卷 / 07期

关键词：

D O I：

10.1021/jo050024u

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The intramolecular, nucleophile-catalyzed, aldol lactonization (NCAL) process merges catalytic, asymmetric carbocycle synthesis with beta-lactone synthesis. The application of modified Mukaiyama reagents to this process led to greatly improved conversion and efficiency (70-82% yield) and shorter reaction times with no diminution of enantioselectivity (91-98% ee). The process was extended to several new aldehyde-acid substrates leading to new bicyclic-beta-lactones. This methodology uniquely provides beta-lactone-fused cyclopentanes and cyclohexanes readied for further transformations.

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页码：2835 / 2838

页数：4

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