Synthesis of Enantiomerically Pure 1,2-Disubstituted 2-Selenoamines

Abstract

Optically pure phenylseleno-(S)-2-p-tolylsulfinylbenzylcarbanions react with (S)-N-2-p-tolylsulfinylimines derived from aliphatic and aromatic aldehydes in a highly stereoselective manner affording bis-sulfinylselenoamines, easily transformed into 1-phenyl, 2-aryl (or alkyl)-2-phenylseleno ethylamines by subsequent reactions, which were treatment reactions with t-BuLi and TFA.

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Keywords:

• Benzyl selenyl carbanion
• double asymmetric induction
• remote stereocontrol with sulfoxides
• 1,2-selenoamines

Acknowledgments

Financial support of this work by the Ministerio de Ciencia y Tecnología (CTQ2009-12168) is acknowledged.