In situ enzymatic screening (ISES) of P,N-ligands for Ni(0)-mediated asymmetric intramolecular allylic amination

David B Berkowitz, Weijun Shen, Gourhari Maiti

Research output: Contribution to journalArticle

17 Citations (Scopus)

Abstract

An in situ enzymatic screening (ISES) approach to rapid catalyst evaluation recently pointed to Ni(0) as a new candidate transition metal for intramolecular allylic amination. This led to further exploration of chiral bidentate phosphine ligands for such transformations. Herein, a variety of P,N-ligands are examined for this Ni(0)-chemistry, using a model reaction leading into the vinylglycinol scaffold. On the one hand, an N,N-bis(2-diphenylphosphinoethyl)alkylamine ('PNP') ligand proved to be the fastest ligand yet seen for this Ni(0)-transformation. On the other, phosphinooxazoline (PHOX) ligands of the Pfaltz-Helmchen-Williams variety gave the highest enantioselectivities (up to 51% ee) among P,N-ligands examined.

Original languageEnglish (US)
Pages (from-to)2845-2851
Number of pages7
JournalTetrahedron Asymmetry
Volume15
Issue number18
DOIs
StatePublished - Sep 20 2004

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Amination
Screening
screening
Ligands
ligands
phosphine
Enantioselectivity
phosphines
Scaffolds
Transition metals
Metals
transition metals
chemistry
catalysts
Catalysts
evaluation

ASJC Scopus subject areas

  • Catalysis
  • Physical and Theoretical Chemistry
  • Organic Chemistry
  • Inorganic Chemistry

Cite this

In situ enzymatic screening (ISES) of P,N-ligands for Ni(0)-mediated asymmetric intramolecular allylic amination. / Berkowitz, David B; Shen, Weijun; Maiti, Gourhari.

In: Tetrahedron Asymmetry, Vol. 15, No. 18, 20.09.2004, p. 2845-2851.

Research output: Contribution to journalArticle

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