Me2Zn-Mediated Catalytic Enantio- and Diastereoselective Addition of TosMIC to Ketones

none5siThe 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.mixedKeeri, Abdul Raheem; Gualandi, Andrea; Mazzanti, Andrea; Lewinski, Janusz; Cozzi, Pier GiorgioKeeri, Abdul Raheem; Gualandi, Andrea; Mazzanti, Andrea; Lewinski, Janusz; Cozzi, Pier Giorgi