The behavior of several N-substibuted 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 corresponding N-substituted benzylamino alcohols in good yields. Investigation of the mechanism of this reductive cleavage, with the aid of labeling experiments, showed the intermediate formation of a-tertiary amino-substituted carbanions.
Reductive Cleavage of N-Substituted 2-Aryl- l,3-oxazolidines: Generation of alfa-Amino-Substituted Carbanions / Azzena, Ugo Gavino; Giovanni, Melloni; Cristina, Nigra. - In: JOURNAL OF ORGANIC CHEMISTRY. - ISSN 0022-3263. - (1993), pp. 6707-6711. [10.1021/jo00076a033]
Reductive Cleavage of N-Substituted 2-Aryl- l,3-oxazolidines: Generation of alfa-Amino-Substituted Carbanions
AZZENA, Ugo Gavino;
1993-01-01
Abstract
The behavior of several N-substibuted 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 corresponding N-substituted benzylamino alcohols in good yields. Investigation of the mechanism of this reductive cleavage, with the aid of labeling experiments, showed the intermediate formation of a-tertiary amino-substituted carbanions.I documenti in IRIS sono protetti da copyright e tutti i diritti sono riservati, salvo diversa indicazione.
