ENANTIOSELECTIVE ADDITION OF DIETHYLZINC TO ALDEHYDES CATALYZED BY PYRIDINEOXAZOLINEALCOHOLS

Authors
MACEDO E MOBERG C
Citation
E. Macedo et C. Moberg, ENANTIOSELECTIVE ADDITION OF DIETHYLZINC TO ALDEHYDES CATALYZED BY PYRIDINEOXAZOLINEALCOHOLS, Tetrahedron : asymmetry, 6(2), 1995, pp. 549-558
Citations number
25
Categorie Soggetti
Chemistry Inorganic & Nuclear","Chemistry Inorganic & Nuclear","Chemistry Physical
Journal title
Tetrahedron : asymmetry → ACNP
ISSN journal
09574166
Volume
6
Issue
2
Year of publication
1995
Pages
549 - 558
Database
ISI
SICI code
0957-4166(1995)6:2<549:EAODTA>2.0.ZU;2-K
Abstract
Chiral 2-pyridylcarbinols carrying chiral oxazolyl substituents in the 6-position of the pyridine ring catalyze the enantioselective additio n of diethylzinc to aromatic aldehydes. The absolute configuration of the product alcohol is determined by the configuration at the stereoge nic center bearing the alcohol group, the effect of the oxazoline ring being to increase the stereoselectivity. Attempts to use methyl ether derivatives of the same ligands in the rhodium-catalyzed hydrosilylat ion of acetophenone did not result in any observed enantioselectivity.