title: Enantioselective Bromo-oxycyclization of Silanol.
abstract: Relying on the nucleophilicity of silanol for building up silicon-incorporated scaffold with an enantiopure tetrasubstituted carbon center remains elusive. In this report, asymmetric bromo-oxycyclization of olefinic silanol by using chiral anionic phase-transfer catalyst is described. This protocol provided a facile entry to a wide arrangement of enantiopure benzoxasilole in moderate to excellent enantioselectivities depending on the unique reactivity of bromine/N-benzyl-DABCO complex.
authors.affiliation: Shaanxi Key Laboratory of Natural Products & Chemical Biology, College of Science, Northwest A&F University , 22 Xinong Road, Yangling 712100, Shaanxi, China.|State Key Laboratory of Natural Medicines, Center of Drug Discovery, China Pharmaceutical University , 24 Tongjiaxiang, Nanjing 210009, China.
authors.forename: Zilei
authors.initials: Z
authors.lastname: Xia
authors.affiliation: Shaanxi Key Laboratory of Natural Products & Chemical Biology, College of Science, Northwest A&F University , 22 Xinong Road, Yangling 712100, Shaanxi, China.|State Key Laboratory of Natural Medicines, Center of Drug Discovery, China Pharmaceutical University , 24 Tongjiaxiang, Nanjing 210009, China.
authors.forename: Jiadong
authors.initials: J
authors.lastname: Hu
authors.affiliation: State Key Laboratory of Natural Medicines, Center of Drug Discovery, China Pharmaceutical University , 24 Tongjiaxiang, Nanjing 210009, China.
authors.forename: Zhigao
authors.initials: Z
authors.lastname: Shen
authors.affiliation: State Key Laboratory of Bioorganic & Natural Products Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences , 345 Lingling Lu, Shanghai 200032, China.
authors.forename: Xiaolong
authors.initials: X
authors.lastname: Wan
authors.affiliation: State Key Laboratory of Natural Medicines, Center of Drug Discovery, China Pharmaceutical University , 24 Tongjiaxiang, Nanjing 210009, China.
authors.forename: Qizheng
authors.initials: Q
authors.lastname: Yao
authors.affiliation: State Key Laboratory of Natural Medicines, Center of Drug Discovery, China Pharmaceutical University , 24 Tongjiaxiang, Nanjing 210009, China.
authors.forename: Yisheng
authors.initials: Y
authors.lastname: Lai
authors.affiliation: Shaanxi Key Laboratory of Natural Products & Chemical Biology, College of Science, Northwest A&F University , 22 Xinong Road, Yangling 712100, Shaanxi, China.
authors.forename: Jin-Ming
authors.initials: JM
authors.lastname: Gao
authors.affiliation: Shaanxi Key Laboratory of Natural Products & Chemical Biology, College of Science, Northwest A&F University , 22 Xinong Road, Yangling 712100, Shaanxi, China.|State Key Laboratory of Bioorganic & Natural Products Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences , 345 Lingling Lu, Shanghai 200032, China.
authors.forename: Weiqing
authors.initials: W
authors.lastname: Xie
mesh_terms: D000475:Alkenes / Q000737:chemistry; D002384:Catalysis; D003500:Cyclization; D006842:Hydrocarbons, Brominated / Q000737:chemistry*; D015394:Molecular Structure; D012821:Silanes / Q000138:chemical synthesis* / Q000737:chemistry; D012825:Silicon / Q000737:chemistry; D013237:Stereoisomerism
chemical_list: D000475:Alkenes; D006842:Hydrocarbons, Brominated; D012821:Silanes; C082343:silanol; D012825:Silicon