Tetrahedron

Electrophilic amination of catecholboronate esters formed in the asymmetric hydroboration of vinylarenes

FI Knight, JM Brown, D Lazzari, A Ricci, AJ Blacker

Index: Knight, Frances I.; Brown, John M.; Lazzari, Dario; Ricci, Alfredo; Blacker, A. John Tetrahedron, 1997 , vol. 53, # 33 p. 11411 - 11424

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Citation Number: 25

Abstract

(S)-(4-Methoxyphenyl)-ethyl-1, 3, 2-benzodioxaborole,(S)-1-(4-chlorophenyl) ethyl-1, 3, 2- benzodioxaborole and (S)-1-indanyl-1, 3, 2-benzodioxaborole, intermediates in the catalytic asymmetric hydroboration of 4-chloro-and 4-methoxystyrene, were isolated as pure oils in 75%, 84% and 49% yield respectively. For the first example, amination with N- chloromagnesio-N-methyl-O-trimethylsilylhydroxylamine gave a mixture of (S)-1-(4- ...