Synthesis of Enantiomerically Pure anti-1,2-Diaryl and syn-1,2-Alkylaryl vic-Selenoamines

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• 作者：Jos茅 L. Garc铆a Ruano ; Esther Torrente ; In茅s Alonso ; Mercedes Rodriguez ; Ana M. Mart铆n-Castro ; Alessandro Degl鈥橧nnocenti ; Lucrezia Frateschi ; Antonella Capperucci
• 刊名：The Journal of Organic Chemistry
• 出版年：2012
• 出版时间：February 17, 2012
• 年：2012
• 卷：77
• 期：4
• 页码：1974-1982
• 全文大小：430K
• 年卷期：v.77,no.4(February 17, 2012)
• ISSN：1520-6904

文摘

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 鈭?8 掳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.