Chiral Lewis Acid-Catalyzed Asymmetric Baylis−Hillman Reactions
- 28 December 2002
- journal article
- research article
- Published by American Chemical Society (ACS) in The Journal of Organic Chemistry
- Vol. 68 (3) , 915-919
- https://doi.org/10.1021/jo026318m
Abstract
An effective chiral Lewis acid-catalyzed asymmetric Baylis-Hillman reaction is described. Good to high enantioselectivities were obtained using 3 mol % chiral catalyst. Novel camphor-derived dimerized ligands were prepared from the condensation of (+)-ketopinic acid with the corresponding diamines and hydrazine under acidic conditions. When alpha-naphthyl acrylate was used as a Michael acceptor, the reaction is complete within 20 min with high stereoselectivity and in reasonable chemical yields.Keywords
This publication has 21 references indexed in Scilit:
- Scope and Limitations of Chiral B-[3,5-Bis(trifluoromethyl)phenyl]oxazaborolidine Catalyst for Use in the Mukaiyama Aldol ReactionThe Journal of Organic Chemistry, 2000
- An enantioselective Baylis–Hillman reaction catalyzed by chiral phosphines under atmospheric pressureChemical Communications, 1998
- Asymmetric Baylis–Hillman reactions: catalysis using a chiral pyrrolizidine baseChemical Communications, 1998
- The Asymmetric Baylis−Hillman ReactionJournal of the American Chemical Society, 1997
- First examples of metal and ligand accelerated catalysis of the Baylis–Hillman reactionChemical Communications, 1996
- Catalytic asymmetric synthesis of α-methylene-β-hydroxy-ketonesJournal of the Chemical Society, Chemical Communications, 1995
- Demonstration of the Synthetic Power of Oxazaborolidine-Catalyzed Enantioselective Diels-Alder Reactions by Very Efficient Routes to Cassiol and Gibberellic AcidJournal of the American Chemical Society, 1994
- Synthese und Strukturen von Bis(trietanolamin)lanthanoid‐KomplexenEuropean Journal of Inorganic Chemistry, 1990
- Enantioselective Diels-Alder Additions with New Chiral Lewis Acids Derived from Amino AcidsSynlett, 1990
- New Chiral Lewis Acid Catalysts Prepared from Simple Amino Acids and Their Use in Asymmetric Diels-Alder ReactionsSynlett, 1990