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Simultaneous Induction of Axial and Planar Chirality in Arene–Chromium Complexes by Molybdenum‐Catalyzed Enantioselective Ring‐Closing Metathesis
Author(s) -
Kamikawa Ken,
Arae Sachie,
Wu WeiYi,
Nakamura Chihiro,
Takahashi Tamotsu,
Ogasawara Masamichi
Publication year - 2015
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201500226
Subject(s) - planar chirality , chirality (physics) , enantioselective synthesis , ring closing metathesis , molybdenum , substituent , axial chirality , catalysis , metathesis , chromium , chemistry , stereochemistry , planar , asymmetric induction , crystallography , organic chemistry , chiral symmetry , physics , polymer , quantum mechanics , quark , nambu–jona lasinio model , polymerization , computer graphics (images) , computer science
The molybdenum‐catalyzed asymmetric ring‐closing metathesis of the various C s ‐symmetric (π‐arene)chromium substrates provides the corresponding bridged planar‐chiral (π‐arene)chromium complexes in excellent yields with up to >99 % ee . With a bulky and unsymmetrical substituent, such as N ‐indolyl or 1‐naphthyl, at the 2‐positions of the η 6 ‐1,3‐diisopropenylbenzene ligands, both biaryl‐based axial chirality and π‐arene‐based planar chirality are simultaneously induced in the products. The axial chirality is retained even after the removal of the dicarbonylchromium fragment, and the chiral biaryl/heterobiaryl compounds are obtained with complete retention of the enantiopurity.