Acetoxyl group directed cyclization promoted by SmI2:: Directing group determined stereocomplementarity

被引：12
|
作者：
Kan, T
Hosokawa, S
Nara, S
Tamiya, H
Shirahama, H
Matsuda, F [1 ]
机构：
[1] Hokkaido Univ, Div Mat Sci, Grad Sch Environm Earth Sci, Sapporo, Hokkaido 0600810, Japan
[2] Hokkaido Univ, Fac Sci, Dept Chem, Sapporo, Hokkaido 0600810, Japan
来源：
JOURNAL OF ORGANIC CHEMISTRY | 2004年 / 69卷 / 25期
关键词：
D O I：
10.1021/jo049203m
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
Complete reversal of diastereoselectivity was observed in the SmI2-promoted ketyl-olefin coupling cyclizations of the hydroxy ketone or aldehyde and its acetate. For example, the stereodivergent synthesis of the epimeric five-membered-ring alcohols 2 and 4 has been accomplished through the SmI2-induced ketyl-olefin coupling cyclizations of the 6-hydroxy ketone 1 and delta-acetoxy ketone 3.
引用
收藏
页码：8956 / 8958
页数：3
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