Diastereofacial selectivity in ketene [2+2] cycloaddition to endocyclic enecarbamates bearing a chiral auxiliary. Synthesis of the (-)-Geissman-Waiss lactone

被引：27

作者：

Miranda, PCML ^{[1
]}

Correia, CRD ^{[1
]}

机构：

[1] UNICAMP, Inst Quim, BR-13083970 Campinas, SP, Brazil

来源：

TETRAHEDRON LETTERS | 1999年 / 40卷 / 44期

基金：

巴西圣保罗研究基金会;

关键词：

chiral auxiliaries; enecarbamates; ketenes; Geissman-Waiss lactone;

D O I：

10.1016/S0040-4039(99)01638-X

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The diastereofacial selectivity of enecarbamates bearing a chiral auxiliary was evaluated for the [2+2]cycloaddition with dichloroketenes. Diastereofacial selectivity ranged from zero (bornyl and menthyl) to 60% (Greene's auxiliary and 8-phenylmenthyl). Chromatography separation of the diastereomeric azacyclobutanones derived from the 8-phenylmenthyl enecarbamate permitted an enantiodivergent synthesis of the (-)-Geissman-Waiss lactone, a key intermediate in the synthesis of necine bases. (C) 1999 Elsevier Science Ltd. All rights reserved.

引用

页码：7735 / 7738

页数：4

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