Design and Synthesis of Chiral Diene Ligands for RhI-Catalyzed Enantioselective Arylation of N-DPP-protected Aldimines: Synthesis of the Antifungal Agent Bifonazole

Jin Fong Syu, Huang Ying Lin, Yu Yi Cheng, Yao Chu Tsai, Yi Ching Ting, Ting Shen Kuo, Damodar Janmanchi, Ping Yu Wu, Julian P. Henschke, Hsyueh Liang Wu

研究成果: 雜誌貢獻文章

11 引文 斯高帕斯(Scopus)

摘要

Herein we describe the design and synthesis of a novel family of bifunctional, chiral bicyclo[2.2.1]heptadiene ligands bearing aryl and secondary amido groups, and demonstrate their usefulness in the RhI-catalyzed enantioselective addition reaction of arylboronic acids to N-diphenylphosphinyl (N-DPP)-protected aldimines. Unlike the analogous RhI-catalysts comprising diene ligands substituted with aryl and carboxylic ester groups, or only with aryl groups, the addition reaction proceeded with high stereoselectivity. The protocol tolerated a range of N-DPP-aldimines and arylboronic acids, producing the desired optically active N-DPP-protected amines with yields between 31–99 % and with ee values up to 91–99 %. The synthetic utility of the method was demonstrated by the conversion of N-DPP-protected amine 3 ae into the antifungal agent, bifonazole (13).

原文英語
頁(從 - 到)14515-14522
頁數8
期刊Chemistry - A European Journal
23
發行號58
DOIs
出版狀態已發佈 - 2017 十月 17

ASJC Scopus subject areas

  • Catalysis
  • Organic Chemistry

指紋 深入研究「Design and Synthesis of Chiral Diene Ligands for Rh<sup>I</sup>-Catalyzed Enantioselective Arylation of N-DPP-protected Aldimines: Synthesis of the Antifungal Agent Bifonazole」主題。共同形成了獨特的指紋。

引用此