Studies on the Base-Promoted Enantioselective Aldol Reaction between an (S,S)-2-OXO-2-Propionyl-1,3,2- Oxazaphosphorinane and Benzaldehyde
- 1 February 1993
- journal article
- Published by Taylor & Francis in Phosphorus, Sulfur, and Silicon and the Related Elements
- Vol. 75 (1-4) , 47-50
- https://doi.org/10.1080/10426509308037361
Abstract
The synthesis of an (S,S)-2-oxo-2-propionyl-1,3,2-oxazaphosphorinane, via the condensation of (S)- 1 -N-isopropylbutan-2-ol (3) with methyl dichloro phosphite (CH3OPCl2) followed by the Michaelis-Arbusov condensation reaction with propionyl chloride, will be described. We will also present the results of OUT investigations which describe the nature of the aldol reaction involving the enolate of oxazaphosphorinane 5 with benzaldehyde.Keywords
This publication has 8 references indexed in Scilit:
- Bornane sultam-directed asymmetric synthesis of crystalline, enantiomerically pure syn aldolsJournal of the American Chemical Society, 1990
- Stereoselective aldol reactions via enolates of α-acylphosphonate diestersJournal of the Chemical Society, Chemical Communications, 1990
- Structure-energy relations for the aldol reaction in nonpolar mediaJournal of the American Chemical Society, 1990
- Structure and Reactivity of Lithium Enolates. From Pinacolone to Selective C‐Alkylations of Peptides. Difficulties and Opportunities Afforded by Complex StructuresAngewandte Chemie International Edition in English, 1988
- Carbanion-accelerated Claisen rearrangements. 4. Asymmetric induction via 1,3,2-oxazaphosphorinanesThe Journal of Organic Chemistry, 1987
- Stereoselective Aldol Reactions with α‐Unsubstituted Chiral EnolatesAngewandte Chemie International Edition in English, 1987
- Stereoelectronic effects on the basicity and nucleophilicity of phosphites and phosphates. Ab initio molecular orbital calculations and the .alpha.-effectJournal of the American Chemical Society, 1984
- Conformations of six-membered ring phosphorus heterocycles. I. Ring conformations and phosphorus configurations of isomeric six-membered ring phosphitesJournal of the American Chemical Society, 1970