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Phenyl vs. Ferrocenyl Cyclometallation Selectivity: Diastereoselective Synthesis of an Enantiopure Iridacycle
Author(s) -
Arthurs Ross A.,
Horton Peter N.,
Coles Simon J.,
Richards Christopher J.
Publication year - 2017
Publication title -
european journal of inorganic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.667
H-Index - 136
eISSN - 1099-0682
pISSN - 1434-1948
DOI - 10.1002/ejic.201600904
Subject(s) - chemistry , enantiopure drug , imine , diastereomer , medicinal chemistry , selectivity , stereochemistry , chloride , organic chemistry , catalysis , enantioselective synthesis
Ferrocenyl (Fc) and phenyl (Ph) containing imines FcCH=NCH(R)Ph and FcCH(R)N=CHPh (R = H and Me) were cycloiridated using [Cp*IrCl 2 ] 2 with NaOAc in CH 2 Cl 2 . All resulted in the formation of neutral chloride ligated half‐sandwich iridacycles as a result of ortho ‐phenyl and not alpha‐ferrocenyl C–H activation. The complexes derived from FcCH=NCH(R)Ph (R = H, Me) were obtained as a mixture of E and Z imine isomers, and with R = Me the product obtained from the ( S )‐imine was isolated by recrystallisation as a single diastereoisomer. The configuration was determined by an X‐ray crystal structure analysis as S C , R Ir , E .