A New Family of Cinchona-Derived Amino Phosphine Precatalysts: Application to the Highly Enantio- and Diastereoselective Silver-Catalyzed Isocyanoacetate Aldol Reaction
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- 作者：Filippo Sladojevich ; Andrea Trabocchi ; Antonio Guarna ; Darren J. Dixon
- 刊名：Journal of the American Chemical Society
- 出版年：2011
- 出版时间：February 16, 2011
- 年：2011
- 卷：133
- 期：6
- 页码：1710-1713
- 全文大小：754K
- 年卷期：v.133,no.6(February 16, 2011)
- ISSN：1520-5126
文摘
A new class of readily accessible chiral amino-phosphine precatalysts derived from 9-amino(9-deoxy) epicinchona alkaloids has been developed. In combination with Ag(I) salts, these amino-phosphines performed as effective cooperative Br酶nsted base/Lewis acid catalysts in the asymmetric aldol reaction of isocyanoacetate nucleophiles. Under optimal conditions, high diastereoselectivities (up to 98%) and enantioselectivities (up to 98%) were obtained.