EFFECT OF AGGREGATION ON STEREOCHEMISTRY AND MECHANISM OF ASYMMETRIC OXIDATION OF THE LITHIUM ENOLATE OF METHYL 3,3-DIMETHYLBUTANOATE IN THE SOLID-STATE AND IN SOLUTION

Authors
WEI Y BAKTHAVATCHALAM R JIN XM MURPHY CK DAVIS FA
Citation
Y. Wei et al., EFFECT OF AGGREGATION ON STEREOCHEMISTRY AND MECHANISM OF ASYMMETRIC OXIDATION OF THE LITHIUM ENOLATE OF METHYL 3,3-DIMETHYLBUTANOATE IN THE SOLID-STATE AND IN SOLUTION, Tetrahedron letters, 34(23), 1993, pp. 3715-3718
Citations number
17
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Tetrahedron letters → ACNP
ISSN journal
00404039
Volume
34
Issue
23
Year of publication
1993
Pages
3715 - 3718
Database
ISI
SICI code
0040-4039(1993)34:23<3715:EOAOSA>2.0.ZU;2-5
Abstract
Oxidation of the title enolate by enantiopure (camphorylsulfonyl)oxazi ridines in THF afforded alpha-hydroxyester with 53-73% ee, but the pro duct from the solid state reactions was racemic. The results suggest t hat the enolate exists and reacts as an aggregate in the solid state r eactions.