A mild multistep conversion of n-protected α-amino acids into N-protected β3-amino acids utilizing the Nef reaction

Brad E Sleebs, Nghi H. Nguyen, Andrew B Hughes

Research output: Contribution to journalArticleResearchpeer-review

2 Citations (Scopus)

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.

Original languageEnglish
Article numberST-2012-B0741-L
Pages (from-to)747-751
Number of pages5
JournalSynlett
Volume24
Issue number6
DOIs
Publication statusPublished - 2013
Externally publishedYes

Keywords

  • amino acids
  • amino alcohols
  • amino aldehydes
  • enantioselectivity
  • nucleophilic addition

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