title: Combining NHC-Cu and Brønsted base catalysis: enantioselective allylic substitution/conjugate additions with alkynylaluminum reagents and stereospecific isomerization of the products to trisubstituted allenes.
abstract: All-catalytic route to trisubstituted allenes: The first examples of catalytic enantioselective allylic substitution reactions that involve alkyne-based nucleophiles and lead to products having tertiary stereogenic centers are followed by an exceptionally stereospecific amine-catalyzed isomerization to trisubstituted allenes (see picture; NHC = N-heterocyclic carbene).
authors.affiliation: Department of Chemistry, Merkert Chemistry Center, Boston College, Chestnut Hill, MA 02467, USA.
authors.forename: Jennifer A
authors.initials: JA
authors.lastname: Dabrowski
authors.forename: Fredrik
authors.initials: F
authors.lastname: Haeffner
authors.forename: Amir H
authors.initials: AH
authors.lastname: Hoveyda
mesh_terms: D000466:Alkadienes / Q000737:chemistry*; D000480:Alkynes / Q000737:chemistry*; D000498:Allyl Compounds / Q000737:chemistry*; D017607:Aluminum Compounds / Q000737:chemistry*; D002384:Catalysis; D003300:Copper / Q000737:chemistry*; D008697:Methane / Q000031:analogs & derivatives* / Q000737:chemistry; D013237:Stereoisomerism
chemical_list: D000466:Alkadienes; D000480:Alkynes; D000498:Allyl Compounds; D017607:Aluminum Compounds; C030011:carbene; C025947:propadiene; D003300:Copper; D008697:Methane
keywords: Brønsted bases; N-heterocyclic carbenes; alkynylaluminum reagents; allenes; copper