title: Direct Synthesis of α-Allenols from TMS-Protected Alkynes and Aldehydes Mediated by Tetrabutylammonium Fluoride.
abstract: A unique chemoselective synthesis of α-allenic alcohols is presented. Tetrabutylammonium fluoride (TBAF) mediated this transformation under mild reaction conditions. A range of functional groups is well-tolerated in this reaction, while affording adducts in moderate to excellent yields (48-96 %, average 76 %). Mechanistic studies, including the use of tetrabutylammonium hydroxide (TBAH), revealed that the hydroxide ion can be the responsible for the observed rearrangement.
authors.affiliation: Department of Chemistry and Biochemistry, University of Texas at Arlington, Planetarium Place Room 130, Arlington, TX, 76019, USA.
authors.forename: Xiaojun
authors.identifier: http://orcid.org/0000-0002-9113-1713
authors.initials: X
authors.lastname: Huang
authors.affiliation: Department of Chemistry and Biochemistry, University of Texas at Arlington, Planetarium Place Room 130, Arlington, TX, 76019, USA. bugarin@uta.edu.
authors.forename: Alejandro
authors.identifier: http://orcid.org/0000-0001-8504-355X
authors.initials: A
authors.lastname: Bugarin
keywords: TMS-protected alkynes; aldehydes; heterocycles; tetrabutylammonium fluoride; α-allenols