title: Me2Zn-Mediated Catalytic Enantio- and Diastereoselective Addition of TosMIC to Ketones.
abstract: The first catalytic asymmetric addition of TosMIC to unactivated ketones is presented. A combination of Me2Zn and aminoalcohol catalyst promoted the aldol addition/cyclization reaction to render oxazolines possessing a fully substituted stereocenter with excellent yields (up to 92%), high enantioselectivities (up to 96%), and complete diastereoselectivity. The chiral oxazolines were then used to give, after a straightforward acid hydrolysis, enantioenriched building blocks bearing tertiary alcohol motifs such as hydroxylaldehydes, hydroxylacids, and hydroxylesters without racemization.
authors.affiliation: Dipartimento di Chimica "G: Ciamician", ALMA MATER STUDIORUM, Università di Bologna, Via Selmi 2, 40126, Bologna (Italy).|Faculty of Chemistry, Warsaw University of Technology, Noakowskiego 3, 00-664, Warsaw (Poland).
authors.forename: Abdul Raheem
authors.initials: AR
authors.lastname: Keeri
authors.affiliation: Dipartimento di Chimica "G: Ciamician", ALMA MATER STUDIORUM, Università di Bologna, Via Selmi 2, 40126, Bologna (Italy). andrea.gualandi10@unibo.it.
authors.forename: Andrea
authors.initials: A
authors.lastname: Gualandi
authors.affiliation: Dipartimento di Chimica "Toso Montanari", ALMA MATER STUDIORUM, Università di Bologna, Viale del Risorgimento 4, 40136, Bologna (Italy).
authors.forename: Andrea
authors.initials: A
authors.lastname: Mazzanti
authors.affiliation: Faculty of Chemistry, Warsaw University of Technology, Noakowskiego 3, 00-664, Warsaw (Poland).
authors.forename: Janusz
authors.initials: J
authors.lastname: Lewinski
authors.affiliation: Dipartimento di Chimica "G: Ciamician", ALMA MATER STUDIORUM, Università di Bologna, Via Selmi 2, 40126, Bologna (Italy). piergiorgio.cozzi@unibo.it.
authors.forename: Pier Giorgio
authors.initials: PG
authors.lastname: Cozzi
keywords: Me2Zn; TosMIC; addition reactions; enantioselectivity; ketones