A NOVEL SYNTHESIS OF OPTICALLY-ACTIVE C-2-SYMMETRICAL PYRIDINE-DERIVATIVES - EFFICIENT REACTION OF CHIRAL TRIFLATES WITH 2-PICOLYLLITHIUM REAGENTS

Authors
KOTSUKI H NAKAGAWA Y MORIYA N TATEISHI H OCHI M SUZUKI T ISOBE K
Citation
H. Kotsuki et al., A NOVEL SYNTHESIS OF OPTICALLY-ACTIVE C-2-SYMMETRICAL PYRIDINE-DERIVATIVES - EFFICIENT REACTION OF CHIRAL TRIFLATES WITH 2-PICOLYLLITHIUM REAGENTS, Tetrahedron : asymmetry, 6(5), 1995, pp. 1165-1174
Citations number
28
Categorie Soggetti
Chemistry Inorganic & Nuclear","Chemistry Inorganic & Nuclear","Chemistry Physical
Journal title
Tetrahedron : asymmetry → ACNP
ISSN journal
09574166
Volume
6
Issue
5
Year of publication
1995
Pages
1165 - 1174
Database
ISI
SICI code
0957-4166(1995)6:5<1165:ANSOOC>2.0.ZU;2-R
Abstract
A variety of optically active CZ-symmetric pyridine derivatives have b een prepared from L- or D-tartaric acid as a chiral source via efficie nt coupling reactions of triflates with 2-picolyllithium reagents, and the utility of 17 and 18 as chiral ligands in the catalytic enantiose lective addition of diethylzinc to benzaldehyde has been demonstrated (up to 41% ee). The synthetic procedure for the corresponding meso-iso mer was also described.