Development and Analysis of a Pd(0)-Catalyzed Enantioselective 1,1-Diarylation of Acrylates Enabled by Chiral Anion Phase Transfer

详细信息    查看全文

• 作者：Eiji Yamamoto ; Margaret J. Hilton ; Manuel Orlandi ; Vaneet Saini ; F. Dean Toste ; Matthew S. Sigman
• 刊名：Journal of the American Chemical Society
• 出版年：2016
• 出版时间：December 14, 2016
• 年：2016
• 卷：138
• 期：49
• 页码：15877-15880
• 全文大小：476K
• ISSN：1520-5126

文摘

Enantioselective 1,1-diarylation of terminal alkenes enabled by the combination of Pd catalysis with a chiral anion phase transfer (CAPT) strategy is reported herein. The reaction of substituted benzyl acrylates with aryldiazonium salts and arylboronic acids gave the corresponding 3,3-diarylpropanoates in moderate to good yields with high enantioselectivies (up to 98:2 er). Substituents on the benzyl acrylate and CAPT catalyst significantly affect the enantioselectivity, and multidimensional parametrization identified correlations suggesting structural origins for the high stereocontrol.