Following an ISES lead

The first examples of asymmetric Ni(0)-mediated allylic amination

David B Berkowitz, Gourhari Maiti

Research output: Contribution to journalArticle

61 Citations (Scopus)

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

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Phosphines
Amination
phosphines
Screening
Bearings (structural)
screening
enzyme inhibitors
Gadiformes
Chirality
Enzyme Inhibitors
chirality
entry
manipulators
Derivatives
catalysts
Catalysts
Substrates
synthesis
Lead
vinylglycine

ASJC Scopus subject areas

  • Biochemistry
  • Physical and Theoretical Chemistry
  • Organic Chemistry

Cite this

Following an ISES lead : The first examples of asymmetric Ni(0)-mediated allylic amination. / Berkowitz, David B; Maiti, Gourhari.

In: Organic Letters, Vol. 6, No. 16, 05.08.2004, p. 2661-2664.

Research output: Contribution to journalArticle

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