Very high regioselective 1,2-addition of organolithiums to α,α-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.
Highly regioselective control of 1,2-addition of organolithiums to α,β-unsaturated compounds promoted by lithium bromide in 2-methyltetrahydrofuran : A facile and eco-friendly access to allylic alcohols and amines / V. Pace, L. Castoldi, P. Hoyos, J.V. Sinisterra, M. Pregnolato, M.J. Sanchez-Montero. - In: TETRAHEDRON. - ISSN 0040-4020. - 67:14(2011 Apr 08), pp. 2670-2675. [10.1016/j.tet.2011.01.067]
Highly regioselective control of 1,2-addition of organolithiums to α,β-unsaturated compounds promoted by lithium bromide in 2-methyltetrahydrofuran : A facile and eco-friendly access to allylic alcohols and amines
L. Castoldi;
2011
Abstract
Very high regioselective 1,2-addition of organolithiums to α,α-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.
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