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

Tetrahedron, Asymmetry
David B BerkowitzGourhari Maiti

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.

Citations

Dec 15, 2017·Current Protocols in Chemical Biology·Robert A Swyka, David B Berkowitz
Nov 23, 2006·Angewandte Chemie·Ramón Gómez ArrayásJuan Carlos Carretero
Oct 31, 2007·Angewandte Chemie·Zhan Lu, Shengming Ma
Dec 2, 2015·Advanced Synthesis & Catalysis·Gregory A Applegate, David B Berkowitz
Mar 20, 2006·Tetrahedron, Asymmetry·David B BerkowitzJill M McFadden
Sep 4, 2009·Journal of Fluorine Chemistry·David B BerkowitzChristopher D McCune
Jun 16, 2005·Journal of the American Chemical Society·Sangeeta DeyDavid B Berkowitz

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