Citation
Jh. Bailey et al., On the diastereoselectivity of alkylations of bicyclic lactams, J CHEM S P1, (12), 2000, pp. 1977-1982
Citations number
58
Categorie Soggetti
Chemistry & Analysis","Organic Chemistry/Polymer Science
Journal title
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1
ISSN journal
14704358
→ ACNP
Issue
12
Year of publication
2000
Pages
1977 - 1982
Database
ISI
SICI code
1470-4358(2000):12<1977:OTDOAO>2.0.ZU;2-B
Abstract
The diastereoselectivity in the alkylation of the enolates of bicyclic lact
ams 2 derived from pyroglutaminol 1a has been found to depend upon the natu
re of the hemiaminal ether protecting group. Although exo-alkylation has be
en widely reported for 2a,b,e, endo-alkylation is favoured for 2d. It is po
stulated that this is a result of the opening of the bicyclic structure of
the enolate derived from 2d, and the consequent stereoelectronic facilitati
on of endo-facial attack.