title: Completely OH-selective FeCl3-catalyzed Prins cyclization: highly stereoselective synthesis of 4-OH-tetrahydropyrans.
abstract: The completely OH-selective Prins cyclization has been realized from the enantioselective ene reaction product. A variety of 4-hydroxyl-tetrahydropyrans were exclusively generated via FeCl(3)-catalyzed Prins reaction. Excellent stereoselectivities (up to >99:1 dr and >99.5:0.5 er) were obtained for a remarkably broad range of substrates under mild reaction conditions. The control experiments, including NOE effects and (18)O-labeling studies, as well as DFT calculations were conducted to provide fundamental insights into the mechanism of the reaction. A different [2 + 2] cycloaddition process was suggested to rationalize the observed OH-selectivity.
authors.affiliation: Key Laboratory of Green Chemistry & Technology, Ministry of Education, College of Chemistry, Sichuan University, Chengdu 610064, People's Republic of China.
authors.forename: Ke
authors.initials: K
authors.lastname: Zheng
authors.forename: Xiaohua
authors.initials: X
authors.lastname: Liu
authors.forename: Song
authors.initials: S
authors.lastname: Qin
authors.forename: Mingsheng
authors.initials: M
authors.lastname: Xie
authors.forename: Lili
authors.initials: L
authors.lastname: Lin
authors.forename: Changwei
authors.initials: C
authors.lastname: Hu
authors.forename: Xiaoming
authors.initials: X
authors.lastname: Feng
mesh_terms: D000438:Alcohols / Q000737:chemistry; D000447:Aldehydes / Q000737:chemistry; D002384:Catalysis; D002712:Chlorides / Q000737:chemistry*; D003500:Cyclization; D005290:Ferric Compounds / Q000737:chemistry*; D006878:Hydroxides / Q000737:chemistry*; D015394:Molecular Structure; D011714:Pyrans / Q000138:chemical synthesis* / Q000737:chemistry; D011789:Quantum Theory; D013237:Stereoisomerism
chemical_list: D000438:Alcohols; D000447:Aldehydes; D002712:Chlorides; D005290:Ferric Compounds; D006878:Hydroxides; D011714:Pyrans; C031356:hydroxide ion; C024555:ferric chloride