ASYMMETRIC MICHAEL-ADDITION AND DERACEMIZATION OF ENOLATE BY CHIRAL CROWN-ETHER

Authors
TOKE L BAKO P KESERU GM ALBERT M FENICHEL L
Citation
L. Toke et al., ASYMMETRIC MICHAEL-ADDITION AND DERACEMIZATION OF ENOLATE BY CHIRAL CROWN-ETHER, Tetrahedron, 54(1-2), 1998, pp. 213-222
Citations number
40
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Tetrahedron → ACNP
ISSN journal
00404020
Volume
54
Issue
1-2
Year of publication
1998
Pages
213 - 222
Database
ISI
SICI code
0040-4020(1998)54:1-2<213:AMADOE>2.0.ZU;2-N
Abstract
Crown ethers anellated to glucose units have been used to catalyse the enantioselective Michael addition of methyl phenylacetate to methyl a crylate in high chemical yields in up to 84% enantiomeric excess. A no vel CH-acid deracemization has also been discovered and the mechanisti c rationale of the asymmetric induction is discussed. The proposed mec hanism of the addition was also substantiated by molecular mechanics c alculations. (C) 1997 Elsevier Science Ltd. All rights reserved.