Preparation of N-protected allylic amines and α-methylene-β-amino acids from vinylalumination/Baylis–Hillman products via tandem SN 2′ substitution–Overman …

PV Ramachandran, TE Burghardt, MVR Reddy

Index: Ramachandran, P. Veeraraghavan; Burghardt, Thomas E.; Reddy, M. Venkat Ram Tetrahedron Letters, 2005 , vol. 46, # 12 p. 2121 - 2124

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Citation Number: 15

Abstract

SN2′ reaction on the acetates obtained from vinylalumination or Baylis–Hillman products, followed by in situ reduction afforded allylic alcohols. Upon conversion to trichloroacetimidates and [3, 3]-sigmatropic rearrangement, the corresponding N-protected β- substituted allylic amines were obtained in good yields. Utilization of hydroxy group as the nucleophile furnished allylic hydroxy esters, which were converted to protected α- ...