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

Research output: Contribution to journalArticle

9 Citations (Scopus)

Abstract

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).

Original languageEnglish
Pages (from-to)14515-14522
Number of pages8
JournalChemistry - A European Journal
Volume23
Issue number58
DOIs
Publication statusPublished - 2017 Oct 17

Keywords

  • 1,2-addition reactions
  • arylboronic acids
  • bifonazole
  • phosphinylaldimines
  • rhodium

ASJC Scopus subject areas

  • Catalysis
  • Organic Chemistry

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