Tetrahedron letters

'Counter-intuitive'regioselectivity, subtle steric and solvation effects in lithiation of cyclic tertiary aralkylamines

…, P Venugopalan, A Kaur, M Mahendru, R Kapoor

Index: Kessar, Satinder V.; Singh, Paramjit; Singh, Kamal Nain; Venugopalan; Kaur, Amarjit; Mahendru, Manu; Kapoor, Rajiv Tetrahedron Letters, 2005 , vol. 46, # 39 p. 6753 - 6755

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Citation Number: 9

Abstract

Lithiation of a series of cyclic aralkyl tertiary amines with sec-BuLi in various solvents has been studied. There is a subtle sensitivity to steric factors and lithium coordinating solvents/additives have an adverse effect. ortho-Lithiation is observed only in the case of an eight-membered cyclic amine and the ease of benzylic lithiation with respect to nitrogen is in the surprising order γ> β≫ α, δ. These observations are discussed in the context of ...