Enantioselective MSPV reduction of ketimines using 2-propanol and (BINOL)Al(III)

Organic Letters
Christopher R GravesSonbinh T Nguyen

Abstract

[reaction: see text] A highly enantioselective Meerwein-Schmidt-Ponndorf-Verley (MSPV) reduction of N-phosphinoyl ketimines by (BINOL)Al(III)/2-propanol is reported. Yields ranging between 79 and 85% with high enantiomeric excesses (93-98%) are observed for a wide range of structurally diverse ketimines. A [2.0.4] bicyclic chelation model is proposed to account for this high selectivity.

Citations

Oct 7, 2006·Chemistry : a European Journal·Ralf J KloetzingPaul Knochel
Oct 31, 2008·Angewandte Chemie·Dominik KoszelewskiWolfgang Kroutil
Feb 14, 2008·Angewandte Chemie·Robert B LettanKarl A Scheidt
Aug 31, 2016·Topics in Current Chemistry·Martin Wills
Jun 10, 2009·Journal of the American Chemical Society·Robert B LettanKarl A Scheidt
Nov 18, 2017·The Journal of Organic Chemistry·Elisabet SelvaDavid Guijarro
Aug 27, 2019·The Journal of Organic Chemistry·Chris Sang Gyu SeoRobert H Morris

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