REDUCTIVE CLEAVAGE OF N-SUBSTITUTED 2-ARYL-1,3-OXAZOLIDINES - GENERATION OF ALPHA-AMINO-SUBSTITUTED CARBANIONS

Authors
AZZENA U MELLONI G NIGRA C
Citation
U. Azzena et al., REDUCTIVE CLEAVAGE OF N-SUBSTITUTED 2-ARYL-1,3-OXAZOLIDINES - GENERATION OF ALPHA-AMINO-SUBSTITUTED CARBANIONS, Journal of organic chemistry, 58(24), 1993, pp. 6707-6711
Citations number
29
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Journal of organic chemistry → ACNP
ISSN journal
00223263
Volume
58
Issue
24
Year of publication
1993
Pages
6707 - 6711
Database
ISI
SICI code
0022-3263(1993)58:24<6707:RCON2->2.0.ZU;2-C
Abstract
The behavior of several N-substituted 2-aryl-1,3-oxazolidines has been investigated under conditions of electron transfer from alkali metals in aprotic solvents. The reduction led to the regioselective cleavage of the benzylic carbon-oxygen bond, with formation of the correspondi ng N-substituted benzylamino alcohols in good yields. Investigation of the mechanism of this reductive cleavage, with the aid of labeling ex periments, showed the intermediate formation of alpha-tertiary amino-s ubstituted carbanions.