ASYMMETRIC SYNTHESIS OF δ-OXOCARBOXYLIC ACIDS BY THE MICHAEL REACTION USING (2R,3S)-3,4-DIMETHYL-5,7-DIOXO-2-PHENYLPERHYDRO-1,4-OXAZEPINE
- 5 May 1978
- journal article
- research article
- Published by Oxford University Press (OUP) in Chemistry Letters
- Vol. 7 (5) , 461-464
- https://doi.org/10.1246/cl.1978.461
Abstract
(2R,3S)-3,4-Dimethyl-5,7-dioxo-2-phenylperhydro-1,4-oxazepine (I) was prepared from methyl hydrogen malonate and l-ephedrine hydrochloride using 2-chloro-1-methylpyridinium tosylate as a coupling reagent. The Michael reaction of (I) to 2-cyclopenten-1-one catalyzed by 1,8-diazabicyclo(5.4.0)undec-7-ene (DBU), followed by hydrolysis and decarboxylation gave highly optically pure 3-cyclopentanoneacetic acid.Keywords
This publication has 5 references indexed in Scilit:
- Oxidation‐Reduction CondensationAngewandte Chemie International Edition in English, 1976
- 1,4-Addition of organometallic reagents to .alpha.,.beta.-unsaturated ketones in the presence of (-)-sparteineThe Journal of Organic Chemistry, 1972
- Solvent effect in a partial asymmetric synthesis—ITetrahedron, 1968
- Asymmetric Synthesis with Sugar Derivatives. I. The Conjugate Additions of Grignard Reagents to α, β-Unsaturated Esters of Sugar DerivativesBulletin of the Chemical Society of Japan, 1966
- N(Im)-Carbobenzoxyhistidine Derivatives as Intermediates for the Synthesis of Histidine Peptides1The Journal of Organic Chemistry, 1962