(-)-8-Phenylmenthyl Acrylate as Chiral Inducer in the Baylis-Hillman Reaction
- 1 May 1993
- journal article
- research article
- Published by Taylor & Francis in Synthetic Communications
- Vol. 23 (9) , 1215-1228
- https://doi.org/10.1080/00397919308011206
Abstract
8-Phenylmenthol 1 is used as a chiral auxiliary in the Baylis-Hillman reaction using a range of aldehydes as substrate. Best results (70% d. e.) are obtained when the reaction is rapid, as is the case with trichloroacetaldehyde.Keywords
This publication has 9 references indexed in Scilit:
- Synthesis, resolution and assignment of absolute configuration of 2-(α-hydroxy)aryl acrylate estersTetrahedron: Asymmetry, 1992
- The ‘Baylis - Hillman Reaction’ mechanism and applications revisitedTetrahedron, 1992
- Asymmetric induction in the Baylis-Hillman reactionTetrahedron: Asymmetry, 1991
- Chiral acrylates as substrates in baylis-hillman reactionTetrahedron Letters, 1990
- Functionalisation of the α position of acrylate systems by the addition of carbonyl compounds: Highly pressure-dependent reactions.Tetrahedron Letters, 1986
- Enantioselective synthesis of .beta.-amino esters through high pressure-induced addition of amines to .alpha.,.beta.-ethylenic estersJournal of the American Chemical Society, 1986
- Enantioselective Michael reactions. Stereoselective addition of enolates of phenmenthol esters to crotonatesTetrahedron Letters, 1985
- High Asymmetric Induction in Lewis Acid‐Promoted Intramolecular Ene‐Type Reactions: A diastereo‐ and enantioselective synthesis of (+)‐α‐allokainic acid. Preliminary CommunicationHelvetica Chimica Acta, 1980
- Preparation of an optically active prostaglandin intermediate via asymmetric inductionJournal of the American Chemical Society, 1975