title: Chirality transfer in Au-catalyzed cyclization reactions of monoallylic diols: selective access to specific enantiomers based on olefin geometry.
abstract: The gold(I)-catalyzed cyclization of monoallylic diols to form tetrahydropyrans is shown to be highly stereoselective when chiral allylic alcohols are employed. Substrates that differ only in olefin geometry provide enantiomeric products from formal S(N)2' reactions in high yields with excellent chirality transfer. The allylic alcohol stereochemistry also efficiently controls the facial selectivity when the substrates include additional stereocenters.
authors.affiliation: Department of Chemistry, University of Florida, Gainesville, Florida 32611, United States. aponick@chem.ufl.edu
authors.forename: Aaron
authors.initials: A
authors.lastname: Aponick
authors.forename: Berenger
authors.initials: B
authors.lastname: Biannic
mesh_terms: D000475:Alkenes / Q000737:chemistry*; D002384:Catalysis; D020650:Combinatorial Chemistry Techniques; D003500:Cyclization; D006046:Gold / Q000737:chemistry*; D015394:Molecular Structure; D020005:Propanols / Q000737:chemistry*; D011714:Pyrans / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism
chemical_list: D000475:Alkenes; D020005:Propanols; D011714:Pyrans; C006463:allyl alcohol; D006046:Gold