Activation of benzylic amines towards regioselective metallation by borane complex formation

MR Ebden, NS Simpkins, DNA Fox

Index: Ebden, Mark R.; Simpkins, Nigel S.; Fox, David N. A. Tetrahedron Letters, 1995 , vol. 36, # 47 p. 8697 - 8700

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Citation Number: 35

Abstract

A solution of BH 3 ·THF (5 ml of a 1M solution in THF, 5 mmol) was added dropwise to a stirred solution of N, N-dimethylbenzylamine (0.675 g, 5 mmol) in THF (20 ml) at 0 °C. The solution was stirred for 30 min at which time TLC (20 % Et 2 O in petroleum ether) showed complete consumption of starting material. The solvent was removed under reduced pressure, and the resulting white solid purified by flash chromatography on silica gel (20 % Et 2 O in petroleum ether as ...