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N-Arylarylideneamines react with sulfinylbenzyl carbanions derived from 2-(p-tolylsulfinyl)toluenes (S)-1 and (S)-2, affording epimeric mixtures at C1 of 1,2-diarylethyl- and 1,2-diarylpropylamine derivatives. The sulfinyl group completely controls the configuration at C2 in the reactions of (S)-2. The configuration at C1 depends on the electron density of the ring adjacent to the iminic carbon atom which is modulated by pi-pi stacking interactions with the ring joined to the carbanionic centre. The stereoselectivity was controlled by modifying the acceptor character of the arylideneamine ring with appropriate substituents, the formation of the highly selective (R) configuration at C1 being made possible by electron-donating groups. N-(2,4,6-Trimethoxyphenyl)arylideneamines have been shown to be suitable starting materials for the preparation of (R)-1,2-diarylethyl- and (1R,2S)-1,2-diarylpropylamines (syn epimers) in a highly stereoselective manner.

Phenylindanes were obtained from the reaction of N-acyl-1-arylalkylamines with polyphosphoric ester (PPE). cis-1-Methyl-3-(3,4-dimethoxyphenyl)-5,6-dimethoxyindane was synthesized to determine which stereoisomer was produced by N-formyl and N-acetyl-1-(3,4-dimethoxyphenyl)ethylamine with PPE. Nuclear magnetic resonance specra (1H and 13C) of several mono-, 1,3-di-, and 1,2,3-tri-substituted indanes were fully analyzed to provide information on steric interactions and conformation of the cyclopentene ring. Possible cyclodimerization pathways are proposed.

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