Tetrahedron Asymmetry p. 1857 - 1868 (1993)
Update date:2022-08-04
Topics:
Koga
Funakoshi
Matsuda
Sakai
Rh(I)(Wilkinson)[ClRh(PPh3)3]-catalyzed cyclization of 6-octen-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 remakably 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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Doi:10.1016/0040-4039(93)88116-Z
(1993)Doi:10.1021/jm00077a009
(1993)Doi:10.1016/0008-6215(93)84248-5
(1993)Doi:10.1021/ol403429e
(2014)Doi:10.1016/S0040-4039(00)60516-6
(1993)Doi:10.1021/ie50532a049
(1954)
