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 language | English |
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Pages (from-to) | 14515-14522 |
Number of pages | 8 |
Journal | Chemistry - A European Journal |
Volume | 23 |
Issue number | 58 |
DOIs | |
Publication status | Published - 2017 Oct 17 |
Keywords
- 1,2-addition reactions
- arylboronic acids
- bifonazole
- phosphinylaldimines
- rhodium
ASJC Scopus subject areas
- Catalysis
- Organic Chemistry
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Dive into the research topics of 'Design and Synthesis of Chiral Diene Ligands for RhI-Catalyzed Enantioselective Arylation of N-DPP-protected Aldimines: Synthesis of the Antifungal Agent Bifonazole'. Together they form a unique fingerprint.Datasets
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CCDC 1983406: Experimental Crystal Structure Determination
Syu, J. (Contributor), Lin, H. (Contributor), Cheng, Y. (Contributor), Tsai, Y. (Contributor), Ting, Y. (Contributor), Kuo, T. (Contributor), Janmanchi, D. (Contributor), Wu, P. (Contributor), Henschke, J. P. (Contributor) & Wu, H. (Contributor), Unknown Publisher, 2020
DOI: 10.5517/ccdc.csd.cc24kwvg, http://www.ccdc.cam.ac.uk/services/structure_request?id=doi:10.5517/ccdc.csd.cc24kwvg&sid=DataCite
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