ENANTIOSELECTIVE SYNTHESIS OF CHIRAL 5-CARBAMOYL-3-PYRIDYL ALCOHOLS BY ASYMMETRIC AUTOCATALYTIC REACTION

Authors
SHIBATA T MORIOKA H TANJI S HAYASE T KODAKA Y SOAI K
Citation
T. Shibata et al., ENANTIOSELECTIVE SYNTHESIS OF CHIRAL 5-CARBAMOYL-3-PYRIDYL ALCOHOLS BY ASYMMETRIC AUTOCATALYTIC REACTION, Tetrahedron letters, 37(48), 1996, pp. 8783-8786
Citations number
16
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Tetrahedron letters → ACNP
ISSN journal
00404039
Volume
37
Issue
48
Year of publication
1996
Pages
8783 - 8786
Database
ISI
SICI code
0040-4039(1996)37:48<8783:ESOC5A>2.0.ZU;2-C
Abstract
A catalytic amount of a chiral zinc alkoxide of 5-carbamoyl-3-pyridyl alkyl alcohol catalyzes an enantioselective alkylation of 5-carbamoylp yridine-3-carbaldehyde by diisopropylzinc to afford itself in up to 86 % e.e. with the same configuration as the catalyst. Enantioselectivity is dependent on the structure of substituents on the nitrogen atom of the amide. Copyright (C) 1996 Elsevier Science Ltd