Preparation of N-protected allylic amines and α-methylene-β- amino acids from vinylalumination/Baylis-Hillman products via tandem S N2′ substitution-Overman rearrangement

P. Veeraraghavan Ramachandran, Thomas E. Burghardt, M. Venkat Ram Reddy

Research output: Contribution to journalArticlepeer-review

16 Scopus citations

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-methylene-β-amino acids via Overman rearrangement.

Original languageEnglish (US)
Pages (from-to)2121-2124
Number of pages4
JournalTetrahedron Letters
Volume46
Issue number12
DOIs
StatePublished - Mar 21 2005

Keywords

  • Allylic alcohols
  • Allylic amines
  • Baylis-Hillman reaction
  • S2′ reaction
  • Vinylalumination
  • β-Amino acids

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