Journal article

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

Brad E Sleebs, Nghi H Nguyen, Andrew B Hughes

SYNLETT | GEORG THIEME VERLAG KG | Published : 2013

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.

University of Melbourne Researchers

Grants

Awarded by NHMRC


Funding Acknowledgements

We thank La Trobe University for the provision of a postgraduate scholarship awarded to N.H.N. and the NHMRC (App. 1010326) for funding B.E.S.