Pd-Catalyzed Asymmetric Synthesis of α-Hydroxy Ketones, Acids and Esters

Tetrasubstituted α-hydroxy carbonyls are common structural motifs present in many building blocks and natural products. In spite of extensive prior work, new asymmetric approaches are still an ongoing challenge. Based on the conditions previously reported for the asymmetric Pd-catalyzed synthesis of quaternary carbon stereocenters, the authors report herein the development of the asymmetric alkylation of dioxanones, which can be efficiently transformed into the corresponding α-hydroxy ketones, acids and esters (up to 93% yield, up to 94% ee). For previous work see: J. T. Mohr, D. C. Behenna, A. M. Harned, B. M. Stoltz Angew. Chem. Int. Ed. 2005, 44, 6924.