title: BF3·OEt2-promoted diastereoselective diacetoxylation of alkenes by PhI(OAc)2.
abstract: Selective syn and anti diacetoxylations of alkenes have been achieved using a PhI(OAc)(2)/BF(3)·OEt(2) system in the presence and absence of water, respectively. A broad range of substrates including electron-deficient alkenes (such as α,β-unsaturated esters) could be elaborated efficiently at room temperature with this methodology, furnishing the desired products in good to excellent yields and diastereoselectivity. In particular, a multigram-scale diastereoselective diacetoxylation of methyl cinnamate (5.00 g) was also accomplished in a few hours, maintaining the same efficiency as small-scale reaction. This novel methodology provides an alternative approach for the preparation of various 1,2-diols.
authors.affiliation: The State Key Laboratory of Natural and Biomimetic Drugs, Department of Chemical Biology, School of Pharmaceutical Sciences, Peking University, Beijing 100191, P. R. China.
authors.forename: Wenhe
authors.initials: W
authors.lastname: Zhong
authors.forename: Jun
authors.initials: J
authors.lastname: Yang
authors.forename: Xiangbao
authors.initials: X
authors.lastname: Meng
authors.forename: Zhongjun
authors.initials: Z
authors.lastname: Li
mesh_terms: D000475:Alkenes / Q000737:chemistry*; D001555:Benzene Derivatives / Q000737:chemistry; D001880:Boranes / Q000737:chemistry; D002384:Catalysis; D060326:Chemistry Techniques, Synthetic; D002934:Cinnamates / Q000737:chemistry; D003500:Cyclization; D004583:Electrons; D004952:Esters / Q000737:chemistry; D017613:Iodine Compounds / Q000737:chemistry; D009682:Magnetic Resonance Spectroscopy; D015394:Molecular Structure; D013237:Stereoisomerism; D014867:Water
chemical_list: D000475:Alkenes; D001555:Benzene Derivatives; D001880:Boranes; D002934:Cinnamates; D004952:Esters; D017613:Iodine Compounds; D014867:Water; C025385:methyl cinnamate; C021274:boron trifluoride