title: Enantio- and diastereoselective assembly of tetrahydrofuran and tetrahydropyran skeletons with all-carbon-substituted quaternary stereocenters.
abstract: Chiral phosphoric acids (HB*) catalyze the asymmetric desymmetrization of meso 1,3-diols through mono-transacetalization with a tethered acetal unit. This new strategy leads to the efficient assembly of tetrahydrofuran and tetrahydropyran skeletons bearing remote all-carbon-substituted quaternary stereocenters that are not straightforward to access by other methods.
authors.affiliation: Department of Chemistry, The Hong Kong University of Science and Technology, Clear Water Bay, Kowloon, Hong Kong SAR (China).
authors.forename: Zhilong
authors.initials: Z
authors.lastname: Chen
authors.forename: Jianwei
authors.initials: J
authors.lastname: Sun
mesh_terms: D000438:Alcohols; D002384:Catalysis; D003500:Cyclization; D005663:Furans / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure; D011714:Pyrans / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism
chemical_list: D000438:Alcohols; D005663:Furans; D011714:Pyrans; C018674:tetrahydrofuran
keywords: asymmetric catalysis; cyclization; organocatalysis; oxygen heterocycles