title: Gold(I)-Catalyzed Enantioselective Desymmetrization of 1,3-Diols through Intramolecular Hydroalkoxylation of Allenes.
abstract: A gold(I)-catalyzed enantioselective desymmetrization of 1,3-diols was achieved by intramolecular hydroalkoxylation of allenes. The catalyst system 3-F-dppe(AuCl)2/(R)-C8-TRIPAg proved to be specifically efficient to promote the desymmetrizing cyclization of 2-aryl-1,3-diols, which have proven challenging substrates in previous reports. Multisubstituted tetrahydrofurans were prepared in good yield with good enantioselectivity and diastereoselectivity by this method.
authors.affiliation: Department of Chemistry, University of California, Berkeley, Berkeley, CA 94720 (USA).
authors.forename: Weiwei
authors.initials: W
authors.lastname: Zi
authors.affiliation: Department of Chemistry, University of California, Berkeley, Berkeley, CA 94720 (USA). fdtoste@berkeley.edu.
authors.forename: F Dean
authors.initials: FD
authors.lastname: Toste
mesh_terms: D000466:Alkadienes / Q000737:chemistry*; D002384:Catalysis; D006046:Gold / Q000737:chemistry*; D013237:Stereoisomerism
chemical_list: D000466:Alkadienes; C025947:propadiene; D006046:Gold
keywords: allenes; desymmetrization; enantioselective synthesis; gold; hydroalkoxylation