Following an ISES lead: The first examples of asymmetric Ni(0)-mediated allylic amination

David B. Berkowitz, Gourhari Maiti

Research output: Contribution to journalArticle

64 Scopus citations

Abstract

An ISES (in situ enzymatic screening) lead pointed to conditions (PMP N-protecting group, Ni(cod)2 catalyst precursor) under which chiral, bidentate phosphines could promote Ni(0)-mediated allylic amination. Therefore, bidentate phosphines bearing central, axial, and planar chirality were examined with two model substrates of interest for PLP-enzyme inhibitor synthesis. In the best case, with (R)-MeO-BIPHEP, vinylglycinol derivative 2 was obtained in 75% ee (97% ee, one recrystallization) from 1. Further manipulation provided a Ni(0)-mediated entry into L-vinylglycine.

Original languageEnglish (US)
Pages (from-to)2661-2664
Number of pages4
JournalOrganic Letters
Volume6
Issue number16
DOIs
StatePublished - Aug 5 2004

ASJC Scopus subject areas

  • Biochemistry
  • Physical and Theoretical Chemistry
  • Organic Chemistry

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