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 |
---|---|
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
Fingerprint
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
-
CCDC 1983406: Experimental Crystal Structure Determination
Syu, J.-F. (Contributor), Lin, H.-Y. (Contributor), Cheng, Y.-Y. (Contributor), Tsai, Y.-C. (Contributor), Ting, Y.-C. (Contributor), Kuo, T.-S. (Contributor), Janmanchi, D. (Contributor), Wu, P.-Y. (Contributor), Henschke, J. P. (Contributor) & Wu, H.-L. (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
Dataset