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Selective Synthesis of Enantiomeric η 6 ‐Arene Chromium Tricarbonyl Complexes with Epimeric Pyrroloimidazolones
Author(s) -
WilsonKonderka Cody,
Doxtator Kathleen,
Metallinos Costa
Publication year - 2016
Publication title -
advanced synthesis and catalysis
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.541
H-Index - 155
eISSN - 1615-4169
pISSN - 1615-4150
DOI - 10.1002/adsc.201600369
Subject(s) - chemistry , epimer , planar chirality , diastereomer , enantiomer , electrophile , chirality (physics) , chromium , stereochemistry , enantioselective synthesis , chiral auxiliary , medicinal chemistry , organic chemistry , catalysis , chiral symmetry , nambu–jona lasinio model , physics , quantum mechanics , quark
A pair of epimeric l ‐proline derived chiral auxiliaries have been developed for the diastereoselective lithiation–substitution of η 6 ‐arene chromium tricarbonyl complexes. Lithiation of the anti epimer affords planar chiral imidazolones in >95:5 dr upon electrophile quench. Application of the same reaction sequence to the syn epimer provides products with opposite planar chirality in equally high levels of diastereomeric purity. The ortho ‐substituted epimeric imidazolones give rise to planar chiral enantiomers upon acid‐induced elimination, thus precluding the need to prepare a d ‐proline‐derived starting material.