Asymmetric Morita−Baylis−Hillman Reactions Catalyzed by Chiral Brønsted Acids
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- 12 September 2003
- journal article
- research article
- Published by American Chemical Society (ACS) in Journal of the American Chemical Society
- Vol. 125 (40) , 12094-12095
- https://doi.org/10.1021/ja037705w
Abstract
Chiral BINOL-derived Brønsted acids catalyze the enantioselective asymmetric Morita−Baylis−Hillman (MBH) reaction of cyclohexenone with aldehydes. The asymmetric MBH reaction requires 2−20 mol % of the chiral Brønsted acid 2e or 2f and triethylphosphine as the nucleophilic promoter. The reaction products are obtained in good yields (39−88%) and high enantioselectivities (67−96% ee). The Brønsted-acid-catalyzed reaction is the first example of a highly enantioselective asymmetric MBH reaction of cyclohexenone with aldehydes.Keywords
This publication has 29 references indexed in Scilit:
- Single enantiomers from a chiral-alcohol catalystNature, 2003
- Chiral Sulfoxides as Neutral Coordinate-Organocatalysts in Asymmetric Allylation of N-Acylhydrazones Using AllyltrichlorosilanesJournal of the American Chemical Society, 2003
- Asymmetric Organocatalysis of 4 + 3 Cycloaddition ReactionsJournal of the American Chemical Society, 2003
- Chiral Lewis Acid-Catalyzed Asymmetric Baylis−Hillman ReactionsThe Journal of Organic Chemistry, 2002
- DYKAT of Baylis−Hillman Adducts: Concise Total Synthesis of Furaquinocin EJournal of the American Chemical Society, 2002
- New Chiral Molybdenum Catalysts for Asymmetric Olefin Metathesis that Contain 3,3‘-Disubstituted Octahydrobinaphtholate or 2,6-Dichlorophenylimido LigandsOrganometallics, 2001
- New Strategies for Organic Catalysis: The First Enantioselective Organocatalytic 1,3-Dipolar CycloadditionJournal of the American Chemical Society, 2000
- New Strategies for Organic Catalysis: The First Highly Enantioselective Organocatalytic Diels−Alder ReactionJournal of the American Chemical Society, 2000
- Catalytic Enantioselective meso-Epoxide Ring Opening Reaction with Phenolic Oxygen Nucleophile Promoted by Gallium Heterobimetallic Multifunctional ComplexesJournal of the American Chemical Society, 2000
- The Asymmetric Baylis−Hillman ReactionJournal of the American Chemical Society, 1997