Tetrahedron

Highly regioselective control of 1, 2-addition of organolithiums to α, β-unsaturated compounds promoted by lithium bromide in 2-methyltetrahydrofuran: a facile and …

…, JV Sinisterra, M Pregnolato, JM Sánchez-Montero

Index: Pace, Vittorio; Castoldi, Laura; Hoyos, Pilar; Sinisterra, Jose Vicente; Pregnolato, Massimo; Sanchez-Montero, Ma. Jose Tetrahedron, 2011 , vol. 67, # 14 p. 2670 - 2675

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Citation Number: 36

Abstract

Very high regioselective 1, 2-addition of organolithiums to α, β-unsaturated carbonyl-like compounds (ketones, aldehydes, and imines) in the presence of LiBr was achieved by carrying out reactions in the sustainable solvent 2-methyltetrahydrofuran. Excellent yields (in isolated product) of allylic alcohols and allylic amines were recovered under a simple experimental procedure at 0° C.