Synthesis of chiral [60]fullerene-steroid bisadducts using steroid templates

被引:38
作者
Ishi-i, T [1 ]
Shinkai, S [1 ]
机构
[1] Japan Sci & Technol Corp JST, Chemotransfigurat Project, Kurume, Fukuoka 8390861, Japan
关键词
D O I
10.1016/S0040-4020(99)00742-5
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The double [4+2] cycloadditions between [60]fullerene and steroid-appended dibenzoates 7 and 8, the reaction sites of which were controlled by diols in chiral template molecules, afforded [60]fullerene-steroid bisadducts 11 and 12 regio- and chiroselectively. CD spectroscopic studies of 11 and 12 indicated that the magnitude of the Cotton effects changes reflecting the chiral structure of the steroid moiety in 11 and 12. (C) 1999 Elsevier Science Ltd. All rights reserved.
引用
收藏
页码:12515 / 12530
页数:16
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