π–π Stacking versus Steric Effects in Stereoselectivity Control: Highly Diastereoselective Synthesis of syn??1, 2??Diarylpropylamines

JL Garcia Ruano, J Alemán, I Alonso…

Index: Garcia Ruano, Jose L.; Aleman, Jose; Alonso, Ines; Parra, Alejandro; Marcos, Vanesa; Aguirre, Jose Chemistry - A European Journal, 2007 , vol. 13, # 21 p. 6179 - 6195

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Citation Number: 40

Abstract

Abstract 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 π–π stacking ...