title: Enantioselective Synthesis of Tertiary Propargylic Alcohols under N-Heterocyclic Carbene Catalysis.
abstract: A straightforward procedure to carry out the enantioselective benzoin reaction between aldehydes and ynones by employing a chiral N-heterocyclic carbene (NHC) as catalyst was developed. Under the optimized reaction conditions, these ynones undergo a clean and selective 1,2-addition with the catalytically generated Breslow intermediate, not observing any byproduct arising from competitive Stetter-type reactivity. This procedure allows the preparation of tertiary alkynyl carbinols as highly enantioenriched materials, which have the remarkable potential to be used as chiral building blocks in organic synthesis.
authors.affiliation: Department of Organic Chemistry II, University of the Basque Country (UPV/EHU), P.O. Box 644, 48080 Bilbao (Spain), Fax: (+34) 94-601-2748.
authors.forename: Eduardo
authors.initials: E
authors.lastname: Sánchez-Díez
authors.affiliation: Department of Organic Chemistry II, University of the Basque Country (UPV/EHU), P.O. Box 644, 48080 Bilbao (Spain), Fax: (+34) 94-601-2748.
authors.forename: Maitane
authors.initials: M
authors.lastname: Fernández
authors.affiliation: Department of Organic Chemistry II, University of the Basque Country (UPV/EHU), P.O. Box 644, 48080 Bilbao (Spain), Fax: (+34) 94-601-2748.
authors.forename: Uxue
authors.initials: U
authors.lastname: Uria
authors.affiliation: Department of Organic Chemistry II, University of the Basque Country (UPV/EHU), P.O. Box 644, 48080 Bilbao (Spain), Fax: (+34) 94-601-2748. efraim.reyes@ehu.es.
authors.forename: Efraim
authors.initials: E
authors.lastname: Reyes
authors.affiliation: Department of Organic Chemistry II, University of the Basque Country (UPV/EHU), P.O. Box 644, 48080 Bilbao (Spain), Fax: (+34) 94-601-2748.
authors.forename: Luisa
authors.initials: L
authors.lastname: Carrillo
authors.affiliation: Department of Organic Chemistry II, University of the Basque Country (UPV/EHU), P.O. Box 644, 48080 Bilbao (Spain), Fax: (+34) 94-601-2748. joseluis.vicario@ehu.es.
authors.forename: Jose L
authors.initials: JL
authors.lastname: Vicario
keywords: alkynes; asymmetric catalysis; carbenes; organocatalysis; umpolung