Journal
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
Volume 133, Issue 40, Pages 15882-15885Publisher
AMER CHEMICAL SOC
DOI: 10.1021/ja2066829
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Funding
- Singapore National Research Foundation [NRF-RF2008-10]
- Nanyang Technological University
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In transition-metal catalyzed, asymmetric alpha-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)-H-8-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.
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