Investigation of the rh-catalyzed asymmetric reductive aldol reaction. Expanded scope based on reaction analysis

Organic Letters
Albert E RussellJames P Morken

Abstract

[reaction: see text] A series of experiments are described that suggest that the Rh-catalyzed reductive aldol reaction proceeds by addition of a Rh(I) hydride, generated in situ, to the reacting acrylate followed by a stereochemistry-controlling aldol addition reaction. On the basis of this hypothesis, reaction conditions are engineered that allow for increased substrate scope.

References

Feb 21, 2002·Journal of the American Chemical Society·Christopher Krug, John F Hartwig
Sep 13, 2002·Journal of the American Chemical Society·Kazuhiro YoshidaTamio Hayashi
Mar 28, 2003·Organic Letters·Ryan R Huddleston, Michael J Krische

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Citations

Jun 20, 2007·Chemical Society Reviews·Hisao Nishiyama
May 31, 2018·Chemical Society Reviews·Yasuhiro YamashitaShū Kobayashi
Jan 12, 2010·Chemistry, an Asian Journal·Shingo HataMakoto Shimizu
Oct 3, 2014·Chemical & Pharmaceutical Bulletin·Motoyuki IsodaAkira Ando
Oct 30, 2013·Chemistry : a European Journal·Andreas KolbPaultheo von Zezschwitz
Oct 9, 2009·Organic Letters·Claire L OswaldHon Wai Lam
Dec 22, 2005·Journal of the American Chemical Society·Michael C Willis, Robert L Woodward
Dec 14, 2018·Organic Letters·Bishnupada SatpathiS S V Ramasastry
Apr 13, 2018·Organic Letters·Yvonne C DePorreCorinna S Schindler

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