Enantioselective Nitroaldol Reaction of α-Ketoesters Catalyzed by Cinchona Alkaloids
Top Cited Papers
- 22 December 2005
- journal article
- research article
- Published by American Chemical Society (ACS) in Journal of the American Chemical Society
- Vol. 128 (3) , 732-733
- https://doi.org/10.1021/ja057237l
Abstract
The development of highly enantioselective and general catalytic nitroaldol (Henry) reactions with ketones is a challenging yet desirable task in organic synthesis. In this communication, we report an asymmetric nitroaldol reaction with α-ketoesters catalyzed by a new C6‘−OH cinchona alkaloid catalyst. This is the first highly efficient organocatalytic asymmetric Henry reaction with ketones. This reaction is operationally simple and affords high enantioselectivity as well as good to excellent yield for a broad range of α-ketoesters.Keywords
This publication has 27 references indexed in Scilit:
- Enantioselective Henry Reactions under Dual Lewis Acid/Amine Catalysis Using Chiral Amino Alcohol LigandsAngewandte Chemie International Edition in English, 2005
- Catalytic Enantioselective C−C Bond Forming Conjugate Additions with Vinyl SulfonesJournal of the American Chemical Society, 2005
- Rhenium(I)‐Catalyzed Intramolecular Geminal Carbofunctionalization of Alkynes: Tandem Cyclization of ω‐Acetylenic Dienol Silyl EthersAngewandte Chemie International Edition in English, 2004
- Metal‐Free, Organocatalytic Asymmetric Transfer Hydrogenation of α,β‐Unsaturated AldehydesAngewandte Chemie International Edition in English, 2004
- Chiral Proton Catalysis: A Catalytic Enantioselective Direct Aza-Henry ReactionJournal of the American Chemical Society, 2004
- Designer Chiral Quaternary Ammonium Bifluorides as an Efficient Catalyst for Asymmetric Nitroaldol Reaction of Silyl Nitronates with Aromatic AldehydesJournal of the American Chemical Society, 2003
- Asymmetric Catalytic Aza‐Henry Reactions Leading to 1,2‐Diamines and 1,2‐Diaminocarboxylic AcidsAngewandte Chemie International Edition in English, 2003
- Total Synthesis of (-)-Thiangazole, a Naturally-Occurring HIV-1 InhibitorThe Journal of Organic Chemistry, 1994
- Basic character of rare earth metal alkoxides. Utilization in catalytic carbon-carbon bond-forming reactions and catalytic asymmetric nitroaldol reactionsJournal of the American Chemical Society, 1992
- Synthesis of an analog of tabtoxinine as a potential inhibitor of D-alanine:D-alanine ligase (ADP forming)Journal of Medicinal Chemistry, 1989