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Synthesis of Unsaturated Macrocycles by Ru‐Catalyzed Ring‐Closing Metathesis: A Comparative Study
Author(s) -
Grisi Fabia,
Costabile Chiara,
Grimaldi Anna,
Viscardi Colomba,
Saturnino Carmela,
Longo Pasquale
Publication year - 2012
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201200960
Subject(s) - chemistry , carbene , ruthenium , stereoselectivity , ring closing metathesis , metathesis , catalysis , ring (chemistry) , olefin metathesis , ligand (biochemistry) , stereochemistry , combinatorial chemistry , organic chemistry , polymerization , biochemistry , polymer , receptor
The activity and stereoselectivity of phosphane‐ and N‐heterocyclic carbene (NHC)‐containing ruthenium benzylidene complexes have been evaluated in macrocyclic ring‐closing olefin metathesis to produce unsaturated lactones and lactams. The success of the macrocyclization depends on the nature of the ligand (phosphane or N‐heterocyclic carbene) on the ruthenium center and on the NHC properties. As for stereoselectivity, E / Z ratios seem to be influenced not only by the nature of the ruthenium catalyst but also by the thermodynamic stabilities of the resulting unsaturated macrocycles, as confirmed by theoretical results.