title: Copper catalyzed asymmetric propargylation of aldehydes.
abstract: The highly enantio- and regioselective copper catalyzed asymmetric propargylation of aldehydes with a propargyl borolane reagent is reported. The methodology demonstrated broad functional group tolerance and provided high enantioselectivities for aliphatic, vinyl, and aryl aldehydes. The utility of the TMS homopropargylic alcohols was demonstrated by the facile conversion to a chiral dihydropyranone.
authors.affiliation: Chemical Development, Boehringer Ingelheim Pharmaceuticals Inc., 900 Ridgebury Road/P.O. Box 368, Ridgefield, Connecticut 06877-0368, USA. daniel.fandrick@boehringer-ingelheim.com
authors.forename: Daniel R
authors.initials: DR
authors.lastname: Fandrick
authors.forename: Keith R
authors.initials: KR
authors.lastname: Fandrick
authors.forename: Jonathan T
authors.initials: JT
authors.lastname: Reeves
authors.forename: Zhulin
authors.initials: Z
authors.lastname: Tan
authors.forename: Wenjun
authors.initials: W
authors.lastname: Tang
authors.forename: Andrew G
authors.initials: AG
authors.lastname: Capacci
authors.forename: Sonia
authors.initials: S
authors.lastname: Rodriguez
authors.forename: Jinhua J
authors.initials: JJ
authors.lastname: Song
authors.forename: Heewon
authors.initials: H
authors.lastname: Lee
authors.forename: Nathan K
authors.initials: NK
authors.lastname: Yee
authors.forename: Chris H
authors.initials: CH
authors.lastname: Senanayake
mesh_terms: D000447:Aldehydes / Q000737:chemistry*; D001896:Boron Compounds / Q000737:chemistry*; D002384:Catalysis; D003300:Copper / Q000737:chemistry*; D015394:Molecular Structure; D013237:Stereoisomerism
chemical_list: D000447:Aldehydes; D001896:Boron Compounds; D003300:Copper