1424614-82-3Relevant articles and documents
An enantioselective, intermolecular α-arylation of ester enolates to form tertiary stereocenters
Huang, Zhiyan,Liu, Zheng,Zhou, Jianrong
supporting information; experimental part, p. 15882 - 15885 (2011/11/13)
In transition-metal catalyzed, asymmetric α-arylation of carbonyl compounds, formation of tertiary centers with high enantioselectivity is a longstanding problem, due to easy enolization of the monoarylation products. Herein, we report such examples using a palladium catalyst supported by a new, (R)-H8-BINOL-derived monophosphine. Silyl ketene acetals, together with a weakly basic activator, were used as equivalents of ester anions, and they reacted smoothly with aryl triflates in excellent enantiomeric excess (ee). The usefulness of the reaction was demonstrated in a gram-scale synthesis of (S)-Naproxen in 92% ee.