title: Ruthenium-BINAP Catalyzed Alcohol C-H tert-Prenylation via 1,3-Enyne Transfer Hydrogenation: Beyond Stoichiometric Carbanions in Enantioselective Carbonyl Propargylation.
abstract: The chiral ruthenium complex formed in situ from (TFA)2Ru(CO)(PPh3)2 and (R)-BINAP is found to catalyze the enantioselective C-C coupling of diverse primary alcohols with the 1,3-enyne, TMSC≡CC(Me)═CH2, to form secondary homopropargyl alcohols bearing gem-dimethyl groups. All reagents for this byproduct-free coupling are inexpensive and commercially available, making this protocol a practical alternative to stoichiometric carbanions in enantioselective carbonyl reverse prenylation.
authors.affiliation: University of Texas at Austin , Department of Chemistry, Austin, Texas 78712, United States.
authors.forename: Khoa D
authors.initials: KD
authors.lastname: Nguyen
authors.affiliation: University of Texas at Austin , Department of Chemistry, Austin, Texas 78712, United States.
authors.forename: Daniel
authors.initials: D
authors.lastname: Herkommer
authors.affiliation: University of Texas at Austin , Department of Chemistry, Austin, Texas 78712, United States.
authors.forename: Michael J
authors.initials: MJ
authors.lastname: Krische
mesh_terms: D000438:Alcohols / Q000737:chemistry; D000480:Alkynes / Q000737:chemistry*; D002384:Catalysis; D006865:Hydrogenation; D007202:Indicators and Reagents / Q000737:chemistry; D009281:Naphthalenes / Q000737:chemistry*; D054876:Prenylation; D012428:Ruthenium / Q000737:chemistry*; D013237:Stereoisomerism
chemical_list: D000438:Alcohols; D000480:Alkynes; C406943:BINAP, 2-naphthol; D007202:Indicators and Reagents; D009281:Naphthalenes; D012428:Ruthenium