Enantioselective oxysulfenylation and oxyselenenylation of olefins catalyzed by chiral Brønsted acids
作者: Huan GuanHaining WangDeshun HuangYian Shi
作者单位: 1Beijing National Laboratory for Molecular Sciences, CAS Key Laboratory of Molecular Recognition and Function, Institute of Chemistry, Chinese Academy of Sciences, Beijing 100190, China
2Department of Chemistry, Colorado State University, Fort Collins, CO 80523, United States
刊名: Tetrahedron, 2012, Vol.68 (12), pp.2728-2735
来源数据库: Elsevier Journal
DOI: 10.1016/j.tet.2012.01.006
关键词: SulfenylationSelenenylationThiiranium ionsSeleniranium ionsDesymmetrizationEnantioselective
英文摘要: Abstract(#br)This paper describes Brønsted 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 β-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.
全文获取路径: Elsevier  (合作)
影响因子:2.803 (2012)