Journal of Organic Chemistry p. 6707 - 6711 (1993)
Update date:2022-08-05
Topics:
Azzena, Ugo
Melloni, Giovanni
Nigra, Cristina
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 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 α-tertiary amino-substituted carbanions.
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