A Mild Multistep Conversion of N-Protected alpha-Amino Acids into N-Protected beta(3)-Amino Acids Utilizing the Nef Reaction

Abstract

Current methods of homologation of α-amino acids to β-amino acids have limitations. To overcome these shortfalls the Nef reaction has been utilized in the multistep synthesis of β3-amino acids from α-amino acids. In this approach, N-protected amino aldehydes, easily accessed from α-amino acids, were transformed into the N-protected γ-amino nitroalkanes. The Nef reaction was then used to smoothly convert the nitroalkanes into the corresponding N-protected β3-amino acids without notable racemization. © Georg Thieme Verlag Stuttgart - New York.