1,3-ASYMMETRIC INDUCTION IN HYDRIDE ADDITION-REACTIONS TO BETA-SUBSTITUTED KETONES - A MODEL FOR CHIRALITY TRANSFER

Authors
EVANS DA DART MJ DUFFY JL
Citation
Da. Evans et al., 1,3-ASYMMETRIC INDUCTION IN HYDRIDE ADDITION-REACTIONS TO BETA-SUBSTITUTED KETONES - A MODEL FOR CHIRALITY TRANSFER, Tetrahedron letters, 35(46), 1994, pp. 8541-8544
Citations number
27
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Tetrahedron letters → ACNP
ISSN journal
00404039
Volume
35
Issue
46
Year of publication
1994
Pages
8541 - 8544
Database
ISI
SICI code
0040-4039(1994)35:46<8541:1IIHAT>2.0.ZU;2-E
Abstract
We report the 1,3-asymmetric induction observed in the additions of va rious hydride reagents to beta-substituted ketones. Both the nature of the beta-substituents and the size of the achiral alkyl group attache d to the carbonyl moiety have a significant effect on the direction an d degree of carbonyl diastereofacial selectivity. A revision of Cram's polar model for 1,3-asymmetric induction is proposed to account for t hese results.