INSIGHT INTO RH(I)-CATALYZED CYCLIZATION OF 6-OCTEN-1-ALS WITH A CHIRAL PROTECTING GROUP

被引：8

作者：

KOGA, I ^{[1
]}

FUNAKOSHI, K ^{[1
]}

MATSUDA, A ^{[1
]}

SAKAI, K ^{[1
]}

机构：

[1] KYUSHU UNIV,FAC PHARMACEUT SCI,FUKUOKA 812,JAPAN

来源：

TETRAHEDRON-ASYMMETRY | 1993年 / 4卷 / 08期

关键词：

D O I：

10.1016/S0957-4166(00)80426-7

中图分类号：

O61 [无机化学];

学科分类号：

070301 ; 081704 ;

摘要：

Rh(I)(Wilkinson )[ClRh(PPh3)3]-catalyzed cyclization of 6-octen-1-als with a chiral protecting group at the C2-position afforded only cis-cyclohexanol derivatives, and in the case of C4-position yielded a mixture of cis and trans cyclohexanol. These findings were remarkably different from the case of the C3-position, in which the trans cyclohexanol derivative was obtained. Wilkinson's complex acts as [ClRh(PPh3)3] a Lewis acid, and this bulkier Lewis acid affords higher diastereoselectivity. Rh(I)-catalyzed cyclization of 6-octen-1-al derivatives is not affected by chiral ligands.

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页码：1857 / 1868

页数：12

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