title: Development of Zn-ProPhenol-catalyzed asymmetric alkyne addition: synthesis of chiral propargylic alcohols.
abstract: The development of a general and practical zinc-catalyzed enantioselective alkyne addition methodology is reported. The commercially available ProPhenol ligand (1) has facilitated the addition of a wide range of zinc alkynylides to aryl, aliphatic, and α,β-unsaturated aldehydes in high yield and enantioselectivity. New insights into the mechanism of this reaction have resulted in a significant reduction in reagent stoichiometry, enabling the use of precious alkynes and avoiding the use of excess dimethylzinc. The enantioenriched propargylic alcohols from this reaction serve as versatile synthetic intermediates and have enabled efficient syntheses of several complex natural products.
authors.affiliation: Department of Chemistry, Stanford University, Stanford, CA 94305-5080, USA. bmtrost@stanford.edu
authors.forename: Barry M
authors.initials: BM
authors.lastname: Trost
authors.forename: Mark J
authors.initials: MJ
authors.lastname: Bartlett
authors.forename: Andrew H
authors.initials: AH
authors.lastname: Weiss
authors.forename: Axel Jacobi
authors.initials: AJ
authors.lastname: von Wangelin
authors.forename: Vincent S
authors.initials: VS
authors.lastname: Chan
mesh_terms: D000438:Alcohols / Q000138:chemical synthesis* / Q000737:chemistry*; D000480:Alkynes / Q000138:chemical synthesis / Q000737:chemistry*; D002384:Catalysis; D008024:Ligands; D015394:Molecular Structure; D020005:Propanols / Q000138:chemical synthesis* / Q000737:chemistry*; D013237:Stereoisomerism; D015032:Zinc / Q000737:chemistry*; D017967:Zinc Compounds / Q000737:chemistry*
chemical_list: D000438:Alcohols; D000480:Alkynes; D008024:Ligands; D020005:Propanols; D017967:Zinc Compounds; C028255:propargyl alcohol; D015032:Zinc