I. Nowak, C. George
Sep 1, 2002
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Journal
Journal of Heterocyclic Chemistry
Abstract
Treatment of benzylic amines derived from 2-(acyloxymethyl)-5-nitroindolines with sodium hexamethyl-disilazide leads to dimeric products resulting from deprotonation in the benzylic position, oxidation of the resulting carbanion to radical by the nitroarene moiety of another molecule, and stereoselective radical recombination. Only those two of six possible diastereoisomers are formed in which the recombination takes place from the less hindered face in the more stable conformation of the presumably near-planar radical.