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Planar Chiral Iridium Complexes with the Δ‐TRISPHAT Anion: Toward the First Enantiopure o ‐Quinone Methide π‐Complex
Author(s) -
Moussa Jamal,
Chamoreau Lise Marie,
Amouri Hani
Publication year - 2013
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.22183
Subject(s) - chemistry , enantiopure drug , iridium , enantioselective synthesis , chirality (physics) , diastereomer , quinone methide , stereochemistry , counterion , cationic polymerization , circular dichroism , crystallography , ion , quinone , organic chemistry , chiral symmetry breaking , catalysis , physics , quantum mechanics , quark , nambu–jona lasinio model
We describe the resolution of a planar chiral cationic iridium complex [Cp*Ir(η 5 ‐2‐methyl‐oxodienyl)][OT f] ( 2 ) following the counterion strategy, where anion metathesis by Δ‐TRISPHAT generates the two diastereomers ( pR, pS) ‐[Cp*Ir(η 5 ‐2‐methyl‐oxodienyl)][Δ‐TRISPHAT] ( 3a , 3a' ). Upon fractional crystallization both compounds were separated as confirmed by 1 H nuclear magnetic resonance (NMR) and circular dichroism studies recorded in solution. The latter represents the key‐complex precursors for the enantioselective synthesis of metallated o ‐quinone methide complexes ( 4a , 4a' ). Chirality 25:449–454, 2013 . © 2013 Wiley Periodicals, Inc.