Tetrahedron

Copper-catalyzed reactions of organotitanium reagents. Highly selective SN 2′-allylation and conjugate addition

M Arai, BH Lipshutz, E Nakamura

Index: Arai, Masayuki; Lipshutz, Bruce H.; Nakamura, Eiichi Tetrahedron, 1992 , vol. 48, # 27 p. 5709 - 5718

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Citation Number: 34

Abstract

In the presence of a catalytic amount of CuI· 2LiCl, alkyltitanium (RTi (Oi-Pr) 3) and titanate reagents (RnTi (Oi-Pr) 5− nLi) undergo highly selective SN2′-alkylation reactions with allylic chlorides and allylic diethylphosphates in high yields. The regioselectivity of the reaction is as high as 99.8%. The reaction proceeds with excellent anti-stereoselectivity with respect to the nucleophile and the leaving group, and exhibits high 1, 2-anti- ...