CONTROL OF RING-JUNCTION STEREOCHEMISTRY VIA RADICAL CYCLIZATION - A NEW CONSTRUCTION OF TRANS-HYDRINDANS

被引:40
作者
SATOH, S [1 ]
SODEOKA, M [1 ]
SASAI, H [1 ]
SHIBASAKI, M [1 ]
机构
[1] HOKKAIDO UNIV,FAC PHARMACEUT SCI,SAPPORO,HOKKAIDO 060,JAPAN
关键词
D O I
10.1021/jo00007a004
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Treatment of 7b with Bu3SnH in toluene containing Et3B at -30-degrees-C afforded trans-hydrindan 8b exclusively (97% yield, trans:cis = 100:0). Furthermore, exposure of 13a to Bu3SnH in the presence of Et3B at -30-degrees-C gave the trans angularly methylated hydrindan 14a in a highly stereocontrolled manner (87% yield, trans:cis = 95:5).
引用
收藏
页码:2278 / 2280
页数:3
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