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Co(II)‐salen catalyzed stereoselective cyclopropanation of fluorinated styrenes
Author(s) -
Tai Serene,
Maskrey Taber S.,
Nyalapatla Prasanth R.,
Wipf Peter
Publication year - 2019
Publication title -
chirality
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.43
H-Index - 77
eISSN - 1520-636X
pISSN - 0899-0042
DOI - 10.1002/chir.23144
Subject(s) - cyclopropanation , chemistry , steric effects , ethyl diazoacetate , stereoselectivity , enantiomer , catalysis , enantioselective synthesis , ligand (biochemistry) , chirality (physics) , medicinal chemistry , stereochemistry , combinatorial chemistry , organic chemistry , receptor , biochemistry , nambu–jona lasinio model , chiral symmetry breaking , physics , quantum mechanics , quark
Abstract Three cis ‐selective Co(II)‐salen complexes have been developed for the asymmetric cyclopropanation of para ‐fluorinated styrenes with ethyl diazoacetate. Increasing the steric reach of the C 2 ‐symmetric ligand side chains improved the enantiomeric ratio of the reaction from 28:1 to 66:1. The methodology was exemplified by the gram‐scale synthesis of a lead compound for the treatment of castration‐resistant prostate cancer (CRPC), as well as a structurally related analog.