Tetrahedron

Regioselective aminobromination of terminal alkenes

A Śliwińska, A Zwierzak

Index: Sliwinska, Anna; Zwierzak, Andrzej Tetrahedron, 2003 , vol. 59, # 31 p. 5927 - 5934

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Citation Number: 27

Abstract

The addition of t-butyl N, N-dibromocarbamate (BBC) to a variety of terminal alkenes has been studied. The reaction was spontaneously initiated and proceeded smoothly in refluxing dichloromethane. The N-bromo adducts, formed upon addition, could be reduced in situ with aqueous sodium sulfite to give the corresponding 2-bromo-N-Boc-amines. Immediate deprotection of these compounds with gaseous HCl or p-toluenesulfonic acid afforded 2- ...