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Stereoselective dimerization of benzylic amines derived from indoline
Author(s) -
Nowak Ireneusz,
George Clifford
Publication year - 2002
Publication title -
journal of heterocyclic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.321
H-Index - 59
eISSN - 1943-5193
pISSN - 0022-152X
DOI - 10.1002/jhet.5570390507
Subject(s) - chemistry , deprotonation , stereoselectivity , diastereomer , moiety , carbanion , indoline , molecule , photochemistry , stereochemistry , medicinal chemistry , organic chemistry , catalysis , ion
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.