DIASTEREOSELECTIVE ALLYLATION OF CHIRAL SULFINYL-SUBSTITUTED THIOPHENECARBALDEHYDES WITH A LEWIS-ACID

被引：23

作者：

ARAI, Y ^{[1
]}

SUZUKI, A ^{[1
]}

MASUDA, T ^{[1
]}

MASAKI, Y ^{[1
]}

SHIRO, M ^{[1
]}

机构：

[1] RIGAKU CORP,AKISHIMA,TOKYO 196,JAPAN

来源：

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1 | 1995年 / 22期

关键词：

D O I：

10.1039/p19950002913

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Diastereoselective allylation of the optically active sulfinyl-substituted thiophenecarbaldehydes 3-5 with allyltriphenylstannane in the presence of a Lewis acid has been examined. Allylation of compounds 4 and 5 in the presence of titanium(IV) tetrachloride produced the addition products 11 and 13, respectively, with good diastereoisomeric excesses (de's), whereas in the presence of tin(IV) tetrachloride the corresponding diastereoisomers 12 and 14, respectively, were obtained. Allylation of compound 5 mediated by ytterbium triflate occurred with excellent diastereoselectivity (96% de) under conventional conditions.

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页码：2913 / 2917

页数：5

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