Stereoselective ZrCl4-Catalyzed Mannich-type Reaction of 尾-Keto Esters with Chiral Trifluoromethyl Aldimines

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• 作者：Luca Parise ; Lucio Pellacani ; Fabio Sciubba ; Laura Trulli ; Stefania Fioravanti
• 刊名：Journal of Organic Chemistry
• 出版年：2015
• 出版时间：August 21, 2015
• 年：2015
• 卷：80
• 期：16
• 页码：8300-8306
• 全文大小：414K
• ISSN：1520-6904

文摘

A method for the synthesis of fluorinated 尾鈥?amino 尾-dicarbonyl compounds using a Zr-catalyzed Mannich-type reaction has been developed, starting from N-protected trifluoromethyl aldimines and cyclic or acyclic 尾-keto esters bearing different ester residues. The in situ generated metallic complex reacted with optically pure trifluoromethyl aldimine derived from (R)-伪-methylbenzylamine, giving a highly diastereoselective asymmetric Mannich-type addition with formation of a chiral quaternary center. The absolute configuration at the new chiral centers was assigned through two-dimensional nuclear Overhauser effect spectroscopic analysis coupled with computational studies.