(SALEN)CR(III) COMPLEX-PROMOTED ASYMMETRIC ADDITION OF LITHIUM ENOLATE OF ACETOPHENONE TO SYMMETRICAL 1,2-EPOXIDES

Authors
CROTTI P DIBUSSOLO V FAVERO L MACCHIA F PINESCHI M
Citation
P. Crotti et al., (SALEN)CR(III) COMPLEX-PROMOTED ASYMMETRIC ADDITION OF LITHIUM ENOLATE OF ACETOPHENONE TO SYMMETRICAL 1,2-EPOXIDES, Gazzetta chimica italiana, 127(5), 1997, pp. 273-275
Citations number
12
Categorie Soggetti
Chemistry
Journal title
Gazzetta chimica italiana → ACNP
ISSN journal
00165603
Volume
127
Issue
5
Year of publication
1997
Pages
273 - 275
Database
ISI
SICI code
0016-5603(1997)127:5<273:(CAAOL>2.0.ZU;2-W
Abstract
The first example of the enantioselective ring opening of 1,2-epoxides by a ketone enolate is described. Using (R,R)-(salen)Cr(III)X (X=Cl, OTf) complexes 9 and 10 as the chiral Lewis acid (LA), the addition of the lithium enolate of acetophenone, 1, to cyclohexene oxide, 2, and cyclopentene oxide, 3, gave the corresponding gamma-hydroxy ketones (g amma-HKs) 4 and 5 in low to moderate yields and in up to 62-84% ee.