The Journal of organic chemistry

Lewis Acid Mediated [2, 3]-Sigmatropic Rearrangement of Allylic α-Amino Amides

J Blid, P Brandt, P Somfai

Index: Blid, Jan; Brandt, Peter; Somfai, Peter Journal of Organic Chemistry, 2004 , vol. 69, # 9 p. 3043 - 3049

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Citation Number: 28

Abstract

Boron trifluoride and BBr3 mediated [2, 3]-sigmatropic rearrangements of allylic α-amino amides have been developed affording secondary amines in good yields.(E)-Crotyl and (E)- cinnamyl α-amino amides 2b and 2c exhibit excellent syn-diastereoselectivity upon rearrangement with either Lewis acid. The allylic amine 2a forms upon treatment with BF3 or BBr3 a five-membered heterocylic complex in which a single halide anion has been ...