Cyclopropanation Reactions Mediated by Group 9 Metal Porphyrin Complexes
- 6 October 2011
- journal article
- review article
- Published by Wiley in European Journal of Inorganic Chemistry
- Vol. 2011 (33) , 5071-5081
- https://doi.org/10.1002/ejic.201100664
Abstract
The one‐pot reaction of diazo compounds with olefins represents a useful strategy to synthesise cyclopropanes, which are important both as starting materials for the synthesis of organic compounds and because of their intrinsic pharmaceutical properties. Herein we describe the catalytic activity of group 9 metal porphyrin complexes to cyclopropanate olefins that present different electronic behaviour. All the most important porphyrin‐based methodologies have been reviewed, stressing the stereocontrol of the reactions achieved in each case. Moreover, mechanism investigations have provided data that can help greatly to elaborate more efficient catalytic systems in the future.Keywords
This publication has 100 references indexed in Scilit:
- Characterization of Tunable Radical Metal–Carbenes: Key Intermediates in Catalytic CyclopropanationOrganometallics, 2011
- First X‐ray Structure of a N‐Naphthaloyl‐Tethered Chiral Dirhodium(II) Complex: Structural Basis for Tether Substitution Improving Asymmetric Control in Olefin CyclopropanationChemistry – A European Journal, 2010
- Construction of Aryliridium−Salen Complexes: Enantio- and Cis-Selective Cyclopropanation of Conjugated and Nonconjugated OlefinsJournal of the American Chemical Society, 2008
- Synthesis of Metal–(Pentadentate‐Salen) Complexes: Asymmetric Epoxidation with Aqueous Hydrogen Peroxide and Asymmetric Cyclopropanation (salenH2: N,N′‐bis(salicylidene)ethylene‐1,2‐diamine)Chemistry – A European Journal, 2007
- Perspective on Dirhodium Carboxamidates as CatalystsThe Journal of Organic Chemistry, 2006
- Manganese and cobalt 3-oxobutylideneaminato complexes: Design and application for enantioselective reactionsScience and Technology of Advanced Materials, 2006
- Electronic and steric effects on the stereoselectivity of cyclopropanation reactions catalysed by rhodium meso-tetraphenylporphyrinsJournal of Molecular Catalysis A: Chemical, 2002
- Homolytic displacements at carbon. Part 8. Synthesis of 1-cyano-2-(trichloroethyl)cyclopropanes from allylcobaloximes via but-3-enylcobaloximes and 1-bromo-1-cyanobut-3-enesJournal of the Chemical Society, Perkin Transactions 1, 1982
- Enantioselective carbenoid cyclopropanation catalyzed by chiral vic-dioximatocobalt(II) complexes prepared from natural camphor and .beta.-pinene. Mechanism and stereochemistryJournal of the American Chemical Society, 1978
- A highly enantioselective synthesis of cyclopropane derivatives through chiral cobalt(II) complex catalyzed carbenoid reaction. General scope and factors determining the enantioselectivityJournal of the American Chemical Society, 1978