Palladium-Catalyzed Enantioselective Decarboxylative Allylic Alkylation of Cyclopentanones

详细信息    查看全文

• 作者：Robert A. Craig II ; Steven A. Loskot ; Justin T. Mohr ; Douglas C. Behenna ; Andrew M. Harned ; Brian M. Stoltz
• 刊名：Organic Letters
• 出版年：2015
• 出版时间：November 6, 2015
• 年：2015
• 卷：17
• 期：21
• 页码：5160-5163
• 全文大小：383K
• ISSN：1523-7052

文摘

The first general method for the enantioselective construction of all-carbon quaternary centers on cyclopentanones by enantioselective palladium-catalyzed decarboxylative allylic alkylation is described. Employing the electronically modified (S)-(p-CF₃)₃-t-BuPHOX ligand, 伪-quaternary cyclopentanones were isolated in yields up to >99% with ee鈥檚 up to 94%. Additionally, in order to facilitate large-scale application of this method, a low catalyst loading protocol was employed, using as little as 0.15 mol % Pd, furnishing the product without any loss in ee.