Tetrahedron letters

Aldol reaction of allenolates generated via 1, 4-addition of iodide anion or its equivalent to α, β-acetylenic ketones

M Taniguchi, T Hino, Y Kishi

Index: Taniguchi, Mikio; Hino, Tohru; Kishi, Yoshito Tetrahedron Letters, 1986 , vol. 27, # 39 p. 4767 - 4770

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Citation Number: 86

Abstract

TMSI, Et 2 AlI and (n-Bu) 4 NI/TiCl 4 smoothly added to α,β-acetylenic ketones in a 1,4-fashion to yield allenolates , which reacted with aldehydes providing aldol adducts in good overall yield. A high Z-stereoselectivity was achieved by use of (n-Bu) 4 NI/TiCl 4 at −78°C, while a high E-stereoselectivity occurred at 0°C. ... Aldol reactions of allenolates, generated via 1,4-addition of an iodide anion equivalent to α,β-unsaturated ketones, are described. A high Z- ...