title: Rapid Asymmetric Synthesis of Disubstituted Allenes by Coupling of Flow-Generated Diazo Compounds and Propargylated Amines.
abstract: We report herein the asymmetric coupling of flow-generated unstabilized diazo compounds and propargylated amine derivatives, using a new pyridinebis(imidazoline) ligand, a copper catalyst and base. The reaction proceeds rapidly, generating chiral allenes in 10-20 minutes with high enantioselectivity (89-98 % de/ee), moderate yields and a wide functional group tolerance.
authors.affiliation: Department of Chemistry, University of Cambridge, Lensfield Road, Cambridge, CB2 1EW, UK.
authors.forename: Jian-Siang
authors.identifier: 0000-0002-6173-8290
authors.initials: JS
authors.lastname: Poh
authors.affiliation: Department of Chemistry, University of Cambridge, Lensfield Road, Cambridge, CB2 1EW, UK.
authors.forename: Szabolcs
authors.initials: S
authors.lastname: Makai
authors.affiliation: Department of Chemistry, University of Cambridge, Lensfield Road, Cambridge, CB2 1EW, UK.
authors.forename: Timo
authors.initials: T
authors.lastname: von Keutz
authors.affiliation: Department of Chemistry, University of Cambridge, Lensfield Road, Cambridge, CB2 1EW, UK.
authors.forename: Duc N
authors.identifier: 0000-0001-7864-2730
authors.initials: DN
authors.lastname: Tran
authors.affiliation: Department of Chemistry, University of Cambridge, Lensfield Road, Cambridge, CB2 1EW, UK.
authors.forename: Claudio
authors.identifier: 0000-0002-4601-8527
authors.initials: C
authors.lastname: Battilocchio
authors.affiliation: UCB Biopharma SPRL, Chemical Research R5, Chemin du Foriest, 1420, Braine-L'Alleud, Belgium.
authors.forename: Patrick
authors.initials: P
authors.lastname: Pasau
authors.affiliation: Department of Chemistry, University of Cambridge, Lensfield Road, Cambridge, CB2 1EW, UK.
authors.forename: Steven V
authors.identifier: 0000-0002-7816-0042
authors.initials: SV
authors.lastname: Ley
keywords: allenes; asymmetric catalysis; copper; diazo compounds; flow chemistry