title: Regioselective allene synthesis and propargylations with propargyl diethanolamine boronates.
abstract: The utility of propargyl diethanolamine boronates as reagents for the preparation of allenes and homopropargylic alcohols is presented. Protonolysis with TFA and electrophilic substitution with N-halosuccinimides proceeded with inversion to provide the corresponding allene in high yield and regioselectivity. Alternatively, the propargylation of aldehydes was achieved with use of the in situ generated lithiated complex.
authors.affiliation: Department of Chemical Development, Boehringer Ingelheim Pharmaceuticals Inc., 900 Old 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: Jonathan T
authors.initials: JT
authors.lastname: Reeves
authors.forename: Zhulin
authors.initials: Z
authors.lastname: Tan
authors.forename: Heewon
authors.initials: H
authors.lastname: Lee
authors.forename: Jinhua J
authors.initials: JJ
authors.lastname: Song
authors.forename: Nathan K
authors.initials: NK
authors.lastname: Yee
authors.forename: Chris H
authors.initials: CH
authors.lastname: Senanayake
mesh_terms: D000466:Alkadienes / Q000138:chemical synthesis* / Q000737:chemistry; D001896:Boron Compounds / Q000737:chemistry*; D002384:Catalysis; D004983:Ethanolamines / Q000737:chemistry*; D015394:Molecular Structure; D013237:Stereoisomerism
chemical_list: D000466:Alkadienes; D001896:Boron Compounds; D004983:Ethanolamines; C025947:propadiene; C020283:diethanolamine