ENANTIOSELECTIVE MUKAIYAMA-MICHAEL REACTIONS OF 2-CARBOMETHOXY CYCLOPENTENONE CATALYZED BY CHIRAL BIS(OXAZOLINE)-CU(II) COMPLEXES

Authors
BERNARDI A COLOMBO G SCOLASTICO C
Citation
A. Bernardi et al., ENANTIOSELECTIVE MUKAIYAMA-MICHAEL REACTIONS OF 2-CARBOMETHOXY CYCLOPENTENONE CATALYZED BY CHIRAL BIS(OXAZOLINE)-CU(II) COMPLEXES, Tetrahedron letters, 37(49), 1996, pp. 8921-8924
Citations number
19
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Tetrahedron letters → ACNP
ISSN journal
00404039
Volume
37
Issue
49
Year of publication
1996
Pages
8921 - 8924
Database
ISI
SICI code
0040-4039(1996)37:49<8921:EMRO2C>2.0.ZU;2-3
Abstract
The conjugate addition of propionate silylketene acetal 1 to 2-carbome thoxy cyclopentenone is promoted by bis(oxazoline)-Cu(II) complexes wi th high diastereoselectivity and good enantiomeric excesses. The absol ute configuration of the product can be controlled by varying the copp er counterion. A catalytic version of the reaction was developed, whic h gave ketoacid 5a in 72% d.e. and 63% e.e. Copyright (C) 1996 Elsevie r Science Ltd