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