Phenylselenyl benzylcarbanion stabilized by an (S)-2-p-tolylsulfinyl group evolves in a highly stereoselective way in the reactions with (S)-N-(p-tolylsulfinyl)imines at -98 degrees C affording diastereomerically pure 1,2-selenoamino derivatives in good yields. The syn or anti relationship of the obtained compounds depends on the alkyl or aryl character of the imine. They are easily transformed into enantiomerically pure (1R,2S)-1-aryl [or (1S,2S)-1-alkyl]-2-(phenylseleno)-2-phenylethylamines by reaction with t-BuLi and subsequent methanolysis of the generated sulfinamide derivatives with TFA.

Synthesis of enantiomerically pure anti-1,2-diaryl and syn-1,2-alkylaryl vic-selenoamines / J. L. García Ruano; E. Torrente; I. Alonso; M. Rodriguez; A. M. Martín-Castro; A. Degl’Innocenti; L. Frateschi; A. Capperucci. - In: JOURNAL OF ORGANIC CHEMISTRY. - ISSN 0022-3263. - ELETTRONICO. - 77:(2012), pp. 1974-1982.

Synthesis of enantiomerically pure anti-1,2-diaryl and syn-1,2-alkylaryl vic-selenoamines

DEGL'INNOCENTI, ALESSANDRO;CAPPERUCCI, ANTONELLA
2012

Abstract

Phenylselenyl benzylcarbanion stabilized by an (S)-2-p-tolylsulfinyl group evolves in a highly stereoselective way in the reactions with (S)-N-(p-tolylsulfinyl)imines at -98 degrees C affording diastereomerically pure 1,2-selenoamino derivatives in good yields. The syn or anti relationship of the obtained compounds depends on the alkyl or aryl character of the imine. They are easily transformed into enantiomerically pure (1R,2S)-1-aryl [or (1S,2S)-1-alkyl]-2-(phenylseleno)-2-phenylethylamines by reaction with t-BuLi and subsequent methanolysis of the generated sulfinamide derivatives with TFA.
2012
77
1974
1982
J. L. García Ruano; E. Torrente; I. Alonso; M. Rodriguez; A. M. Martín-Castro; A. Degl’Innocenti; L. Frateschi; A. Capperucci
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Utilizza questo identificatore per citare o creare un link a questa risorsa: https://hdl.handle.net/2158/605574
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