Catalytic enantioselective allylic amination of olefins for the synthesis of ent -sitagliptin

Hongli Bao, Liela Bayeh, Uttam Tambar

Research output: Contribution to journalArticle

8 Scopus citations

Abstract

The presence of nitrogen atoms in most chiral pharmaceutical drugs has motivated the development of numerous strategies for the synthesis of enantiomerically enriched amines. Current methods are based on multistep transformations of functionalized allylic electrophiles to form chiral allylic amines. The enantioselective allylic amination of nonactivated olefins would represent a more direct and more attractive strategy. We report the enantio selective synthesis of ent-sitagliptin through an allylic amination of a nonactivated terminal olefin.

Original languageEnglish (US)
Article numberST-2013-S0710-L
Pages (from-to)2459-2463
Number of pages5
JournalSynlett
Volume24
Issue number18
DOIs
StatePublished - Oct 24 2013

Keywords

  • aminations
  • asymmetric catalysis
  • drugs
  • palladium
  • rearrangements

ASJC Scopus subject areas

  • Organic Chemistry

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