Claisen rearrangement of allylic alcohols prepared through N-Boc-2-acyloxazolidine methodology.: Application to the synthesis of trisubstituted cyclopropanes

被引：18

作者：

Agami, C ^{[1
]}

Couty, F ^{[1
]}

Evano, G ^{[1
]}

机构：

[1] Univ Paris 06, Lab Synth Asymetr, CNRS, F-75005 Paris, France

来源：

TETRAHEDRON LETTERS | 2000年 / 41卷 / 43期

关键词：

oxazolidines; asymmetric synthesis; Claisen rearrangement; epoxidation;

D O I：

10.1016/S0040-4039(00)01465-9

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Stereodefined allylic alcohols prepared from a (R)-phenylglycinol-derived Weinreb amide undergo a Claisen rearrangement with a high level of stereocontrol. The produced N-Boc-2-alcenyloxazolidines can be either hydrolyzed to afford enantiomerically enriched enals or further epoxidized using a two-step sequence. The resulting epoxyoxazolidines can then be transformed into trisubstituted cyclopropanes. (C) 2000 Elsevier Science Ltd. All rights reserved.

引用

页码：8301 / 8305

页数：5

共 13 条

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