title: Highly enantioselective phenylacetylene additions to both aliphatic and aromatic aldehydes.
abstract: The readily available and inexpensive BINOL in combination with Ti(O(i)Pr)(4) is found to catalyze the reaction of an alkynylzinc reagent with various types of aldehydes including aliphatic aldehydes, aromatic aldehydes, and other alpha,beta-unsaturated aldehydes to generate chiral propargyl alcohols with 91-99% ee at room temperature. No previous chiral catalysts have exhibited such a broad scope of enantioselectivity with respect to the type of aldehydes for this reaction. [reaction: see text]
authors.affiliation: Department of Chemistry, University of Virginia, Charlottesville, VA 22904-4319, USA.
authors.forename: Ge
authors.initials: G
authors.lastname: Gao
authors.forename: David
authors.initials: D
authors.lastname: Moore
authors.forename: Ru-Gang
authors.initials: RG
authors.lastname: Xie
authors.forename: Lin
authors.initials: L
authors.lastname: Pu
mesh_terms: D000114:Acetylene / Q000031:analogs & derivatives* / Q000737:chemistry*; D000447:Aldehydes / Q000138:chemical synthesis* / Q000737:chemistry*; D007202:Indicators and Reagents; D008958:Models, Molecular; D008968:Molecular Conformation; D013237:Stereoisomerism
chemical_list: D000447:Aldehydes; D007202:Indicators and Reagents; C044736:phenylacetylene; D000114:Acetylene