Studies of the regiospecific 3-aza-Cope rearrangement promoted by electrophilic reagents

NS Barta, GR Cook, MS Landis…

Index: Barta, Nancy S.; Cook, Gregory R.; Landis, Margaret S.; Stille, John R. Journal of Organic Chemistry, 1992 , vol. 57, # 28 p. 7188 - 7194

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Citation Number: 25

Abstract

The 3-ma-Cope rearrangement of N-alkyl-N-allyl enamine substrates, which required temperatures of 250 OC to proceed thermally, was promoted at 111 OC in the presence of electrophilic reagents such as HCl (0.5 equiv), TiC1,(0.2 equiv), A1Me3 (1.2 equiv), or (ArO) 2A1Me (1.2 equiv). In order to probe the regioselectivity of this accelerated carbon-carbon bond forming process under these reaction conditions, several enamine substrates were ...