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
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.
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页码:6327 / 6330
页数:4
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