DOUBLE STEREOCONTROL IN ALPHA-ALKYLATION OF CHIRAL LITHIUM DIENOLATESGENERATED FROM (E)-ALPHA,BETA-OLEFINIC AMIDES AND ESTERS

Authors
TOMOOKA K NAGASAWA A NAKAI T
Citation
K. Tomooka et al., DOUBLE STEREOCONTROL IN ALPHA-ALKYLATION OF CHIRAL LITHIUM DIENOLATESGENERATED FROM (E)-ALPHA,BETA-OLEFINIC AMIDES AND ESTERS, Chemistry Letters, (10), 1998, pp. 1049-1050
Citations number
15
Categorie Soggetti
Chemistry
Journal title
Chemistry Letters → ACNP
ISSN journal
03667022
Issue
10
Year of publication
1998
Pages
1049 - 1050
Database
ISI
SICI code
0366-7022(1998):10<1049:DSIAOC>2.0.ZU;2-6
Abstract
The methylation of the lithium dienolate generated from (E)-alpha,beta -olefinic amide with Katsuki's chiral auxiliary affords the alpha-meth ylated beta,gamma-enamide in an exceptionally high Z-selectivity (99%) over the terminal olefinic bond alone with 99% de at the alpha-chiral center. The origin of the high Z-selectivity is discussed.