An Enantioselective, Intermolecular 伪-Arylation of Ester Enolates To Form Tertiary Stereocenters
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- 作者：Zhiyan Huang ; Zheng Liu ; Jianrong (Steve) Zhou
- 刊名：Journal of the American Chemical Society
- 出版年：2011
- 出版时间：October 12, 2011
- 年：2011
- 卷：133
- 期：40
- 页码：15882-15885
- 全文大小：795K
- 年卷期：v.133,no.40(October 12, 2011)
- ISSN：1520-5126
文摘
In transition-metal catalyzed, asymmetric 伪-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.