Chiral Lewis Acid Catalysis in Aqueous Media. Catalytic Asymmetric Aldol Reactions of Silyl Enol Ethers with Aldehydes in a Protic Solvent Including Water
- 1 January 1999
- journal article
- Published by Oxford University Press (OUP) in Chemistry Letters
- Vol. 28 (1) , 71-72
- https://doi.org/10.1246/cl.1999.71
Abstract
Chiral copper(II)-catalyzed asymmetric aldol reactions of silyl enol ethers with aldehydes have been successfully carried out in a water-ethanol solution. The use of the protic solvent including water is essential in these reactions, and this report has proposed and demonstrated a new concept for solvents in catalytic asymmetric aldol reactions.Keywords
This publication has 29 references indexed in Scilit:
- New Catalytic Concepts for the Asymmetric Aldol ReactionChemistry – A European Journal, 1998
- Catalyzed enantioselective aldol additions of latent enolate equivalentsTetrahedron: Asymmetry, 1998
- New types of Lewis acids used in organic synthesisPure and Applied Chemistry, 1998
- Catalytic Asymmetric Aldol Reaction via Chiral Pd(II) Enolate in Wet DMFThe Journal of Organic Chemistry, 1995
- Pronounced Solvent and Concentration Effects in an Enantioselective Mukaiyama Aldol Condensation Using BINOL-Titanium(IV) CatalystsJournal of the American Chemical Society, 1995
- Catalytic, Enantioselective Aldol Additions with Methyl and Ethyl Acetate O-Silyl Enolates: A Chiral Tridentate Chelate as a Ligand for Titanium(IV)Journal of the American Chemical Society, 1994
- Lanthanide Triflates as Water-Tolerant Lewis Acids. Activation of Commercial Formaldehyde Solution and Use in the Aldol Reaction of Silyl Enol Ethers with Aldehydes in Aqueous MediaThe Journal of Organic Chemistry, 1994
- Asymmetric Catalytic Aldol-type Reaction with Ketene Silyl Acetals: Possible Intervention of the Silatropic Ene PathwayJournal of the American Chemical Society, 1994
- Catalytic Enantioselective C-C Coupling—Allyl Transfer and Mukaiyama Aldol ReactionAngewandte Chemie International Edition in English, 1994
- Enantioselective and diastereoselective catalysis of the Mukaiyama aldol reaction: ene mechanism in titanium-catalyzed aldol reactions of silyl enol ethersJournal of the American Chemical Society, 1993