Preparation of N-protected allylic amines and α-methylene-β-amino acids from vinylalumination/Baylis–Hillman products via tandem S_N2′ substitution–Overman rearrangement

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• 作者：Ramachandran ; P. Veeraraghavan ; Burghardt ; Thomas E. ; Reddy ; M. Venkat Ram
• 关键词：脙脙脙脙-Amino acids ; Allylic amines ; S_N2芒芒芒 reaction ; Allylic alcohols ; Vinylalumination ; Baylis脙脙脙脙脙脙Hillman reaction.
• 刊名：Tetrahedron Letters
• 出版年：2005
• 期刊代码：109_00404039
• 类别：ch
• 出版时间：March 21, 2005
• 卷：46
• 期：12
• 页码：2121-2124
• 文件大小：129 K

摘要

S_N2芒芒芒 reaction on the acetates obtained from vinylalumination or Baylis芒芒芒Hillman products, followed by in situ reduction afforded allylic alcohols. Upon conversion to trichloroacetimidates and [3,3]-sigmatropic rearrangement, the corresponding N-protected 芒芒-substituted allylic amines were obtained in good yields. Utilization of hydroxy group as the nucleophile furnished allylic hydroxy esters, which were converted to protected 芒芒-methylene-芒芒-amino acids via Overman rearrangement.