Stereodivergent allylindation of cyclopropenes. Remarkable stereodirection and acceleration by neighbouring carboxyl and hydroxyl groups

被引：47

作者：

Araki, S ^{[1
]}

Nakano, H ^{[1
]}

Subburaj, K ^{[1
]}

Hirashita, T ^{[1
]}

Shibutani, K ^{[1
]}

Yamamura, H ^{[1
]}

Kawai, M ^{[1
]}

Butsugan, Y ^{[1
]}

机构：

[1] Nagoya Inst Technol, Dept Appl Chem, Showa Ku, Nagoya, Aichi 4668555, Japan

来源：

TETRAHEDRON LETTERS | 1998年 / 39卷 / 35期

关键词：

D O I：

10.1016/S0040-4039(98)01343-4

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Stereodivergent allylindation of cyclopropene derivatives has been realised regio- and stereoselectively. The coupling occurs exclusively at the gamma-carbon of allylic indium reagents and the more substituted carbon of the cyclopropene double bond The carboxyl and hydroxymethyl groups on the cyclopropene C-3-carbon exert significant effects in cis-direction and acceleration of the allylindation based on the intramolecular chelation, whereas the ester group directs a trans-addition owing to the steric interaction with incoming allylindium reagents. (C) 1998 Elsevier Science Ltd. All rights reserved.

引用

页码：6327 / 6330

页数：4

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