Premium
Phospholane‐Phosphite Ligands for Rh Catalyzed Enantioselective Conjugate Addition: Unusually Reactive Catalysts for Challenging Couplings
Author(s) -
Gilbert Sophie H.,
Fuentes José A.,
Cordes David B.,
Slawin Alexandra M. Z.,
Clarke Matthew L.
Publication year - 2020
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.202000336
Subject(s) - chemistry , enantioselective synthesis , catalysis , rhodium , conjugate , nucleophile , binap , ligand (biochemistry) , combinatorial chemistry , aryl , boronic acid , organic chemistry , reactive intermediate , acceptor , biochemistry , alkyl , receptor , physics , condensed matter physics , mathematical analysis , mathematics
The use of Rh catalysts derived from a phospholane‐phosphite ligand were found to be more productive than the classic rhodium/BINAP system in enantioselective conjugate additions. These catalysts enable the use of lower amounts of aryl boronic acid in an asymmetric arylation reaction that required an impractical excess of nucleophile. This catalyst was also found to enable the coupling of a poorly reactive Michael acceptor, N ‐CBz‐2‐3‐dehydro‐4‐piperidone, or the coupling of poorly reactive 2‐furyl boronic acids at ambient or near temperatures.