a Dipartimento di Chimica “G: Ciamician”, Università di Bologna, Via Selmi 2, 40126, Bologna, Italy
b Faculty of Chemistry, Warsaw University of Technology, Noakowskiego 3, 00-664, Warsaw, Poland
c Dipartimento di Chimica “Toso Montanari”, Università di Bologna, Viale del Risorgimento 4, 40136, Bologna, Italy
First published online 23 Nov 2015.
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.