Investigation of the Rh-Catalyzed Asymmetric Reductive Aldol Reaction. Expanded Scope Based on Reaction Analysis
- 5 June 2004
- journal article
- Published by American Chemical Society (ACS) in Organic Letters
- Vol. 6 (14) , 2309-2312
- https://doi.org/10.1021/ol049591e
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.Keywords
This publication has 9 references indexed in Scilit:
- Enolate Generation under Hydrogenation Conditions: Catalytic Aldol Cycloreduction of Keto-EnonesOrganic Letters, 2003
- A New Type of Catalytic Tandem 1,4-Addition−Aldol Reaction Which Proceeds through an (Oxa-π-allyl)rhodium IntermediateJournal of the American Chemical Society, 2002
- Catalytic Cycle of Rhodium-Catalyzed Asymmetric 1,4-Addition of Organoboronic Acids. Arylrhodium, Oxa-π-allylrhodium, and Hydroxorhodium IntermediatesJournal of the American Chemical Society, 2002
- Direct Observation of Aldehyde Insertion into Rhodium−Aryl and −Alkoxide ComplexesJournal of the American Chemical Society, 2002
- Rhodium-Catalyzed Enantioselective Reductive Aldol ReactionJournal of the American Chemical Society, 2000
- A mild aldol reaction of aryl aldehydes through palladium-catalyzed hydrosilation of α,β-unsaturated carbonyl compounds with trichlorosilaneTetrahedron Letters, 1998
- Rhodium catalyzed direct coupling of αβ-unsaturated ketone, aldehyde, and trialkylsilane: An easy access to regio-defined aldol derivativesTetrahedron Letters, 1990
- Cobalt(II) Catalyzed Coupling Reaction of α,β-Unsaturated Compounds with Aldehydes by the Use of Phenylsilane. New Method for Preparation of β-Hydroxy Nitriles, Amides, and EstersChemistry Letters, 1989
- Novel synthesis of β-siloxy esters by condensation of carbonyls and trimethylsilane with α,β-unsaturated esters catalyzed by RhCl3Tetrahedron Letters, 1987