Enantioselective [2,3]-sigmatropic and [1,2]-Stevens rearrangements via intramolecular formation of allylic oxonium ylides catalyzed by chiral dirhodium(II) carboxylates

被引：61

作者：

Kitagaki, S ^{[1
]}

Yanamoto, Y ^{[1
]}

Tsutsui, H ^{[1
]}

Anada, M ^{[1
]}

Nakajima, M ^{[1
]}

Hashimoto, S ^{[1
]}

机构：

[1] Hokkaido Univ, Grad Sch Pharmaceut Sci, Sapporo, Hokkaido 0600812, Japan

来源：

TETRAHEDRON LETTERS | 2001年 / 42卷 / 36期

关键词：

rhodium and compounds; ylides; rearrangements; enantio-control; diazo compounds;

D O I：

10.1016/S0040-4039(01)01282-5

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Tandem intramolecular generation and rearrangement of allylic oxonium ylides from oc-diazo P-keto esters has been effected with the aid of dirhodium(II) tetrakis[N-phthaloyl-(S)-tert-leucinate] in toluene, providing benzofuran-3-ones via [2,3]-sigmatropic rearrangement in up to 76% cc. In systems with crotyl and prenyl substituents, products arising from the less common [1,2]-Stevens rearrangement as a side reaction have also been obtained in up to 66% ee. It is suggested that competitive [2,3]- and [1,2]-rearrangements proceed through a common, chiral rhodium(II)-bound oxonium ylide intermediate. (C) 2001 Elsevier Science Ltd. All rights reserved.

引用

页码：6361 / 6364

页数：4

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