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Substrate and Catalyst Effects in the Enantioselective Copper‐Catalysed C–H Insertion Reactions of α‐Diazo‐β‐oxo Sulfones
Author(s) -
Shiely Amy E.,
Clarke LeslieAnn,
Flynn Christopher J.,
Buckley Aoife M.,
Ford Alan,
Lawrence Simon E.,
Maguire Anita R.
Publication year - 2018
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.201800077
Subject(s) - chemistry , diazo , oxazoline , enantioselective synthesis , substrate (aquarium) , catalysis , copper , intramolecular force , ligand (biochemistry) , medicinal chemistry , combinatorial chemistry , organic chemistry , biochemistry , oceanography , receptor , geology
Excellent enantioselectivities of up to 98 % ee are achieved by employing the copper‐bis(oxazoline)‐NaBARF catalyst system in the C–H insertion reactions of α‐diazo‐β‐oxo sulfones. The influence of variation of the bis(oxazoline) ligand, copper salt, additive and substrate on both the efficiency and the enantioselectivities of these intramolecular C–H insertion reactions has been explored. Optimum enantioselectivities are achieved with phenyl and diphenyl ligands across the substrate series.