Enantioselective oxysulfenylation and oxyselenenylation of olefins catalyzed by chiral Br?nsted acids

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• 作者：Huan Guan^a ; Haining Wang^a ; Deshun Huang^a ; Yian Shi^a ; ^b ; ^{yian@lamar.colostate.ed}
• 关键词：Sulfenylation ; Selenenylation ; Thiiranium ions ; Seleniranium ions ; Desymmetrization ; Enantioselective
• 刊名：Tetrahedron
• 出版年：2012
• 出版时间：25 March, 2012
• 年：2012
• 卷：68
• 期：12
• 页码：2728-2735
• 全文大小：483 K

文摘

This paper describes Br?nsted acid catalyzed enantioselective oxysulfenylation and oxyselenenylation of olefins. Enantiomerically enriched tetrahydrofurans are formed with up to 63 % ee with dibenzoyl-d-tartaric acid and its derivatives as catalyst. Chiral ¦Â-carboxyl sulfides and selenides have also been obtained with up to 50 % and 84 % ee, respectively, via enantioselective desymmetrization of thiiranium and seleniranium ions in the presence of catalytic amounts of chiral binaphthol derived N-triflyl phosphoramide.