Carbenoid transfer in competing reactions catalyzed by ruthenium complexes

作者: Ileana Dragutan , Valerian Dragutan , Francis Verpoort

DOI: 10.1002/AOC.3094

关键词: Transition metal carbene complexCarbeneOrganic chemistryCarbenoidChemistryEthyl diazoacetateEnantioselective synthesisCatalysisRutheniumCyclopropanation

摘要: Aiming at improving catalyst activity, ten ruthenium promoters have been investigated in carbenoid transfer from ethyl diazoacetate to styrene as a model substrate. Optimal selectivity cyclopropanation has attained with the new NHC–Ru complex 10, well Fischer carbene 7. The surprising non-metathetical behavior of Grubbs’ first-generation this multifaceted process is highlighted. Copyright © 2014 John Wiley & Sons, Ltd.

参考文章(54)
Hélène Lebel, Jean-François Marcoux, Carmela Molinaro, André B. Charette, Stereoselective Cyclopropanation Reactions Chemical Reviews. ,vol. 103, pp. 977- 1050 ,(2003) , 10.1021/CR010007E
Janis Louie, Robert H. Grubbs, Metathesis of Electron-Rich Olefins: Structure and Reactivity of Electron-Rich Carbene Complexes Organometallics. ,vol. 21, pp. 2153- 2164 ,(2002) , 10.1021/OM011037A
Jun-ichi Ito, Satoshi Ujiie, Hisao Nishiyama, Chiral Bis(oxazolinyl)phenyl RuII Catalysts for Highly Enantioselective Cyclopropanation Chemistry: A European Journal. ,vol. 16, pp. 4986- 4990 ,(2010) , 10.1002/CHEM.200903514
Irène Nicolas, Paul Le Maux, Gérard Simonneaux, Asymmetric catalytic cyclopropanation reactions in water Coordination Chemistry Reviews. ,vol. 252, pp. 727- 735 ,(2008) , 10.1016/J.CCR.2007.09.003
Byung Gyu Kim, Marc L. Snapper, Preparation of Alkenyl Cyclopropanes through a Ruthenium-Catalyzed Tandem Enyne Metathesis--Cyclopropanation Sequence Journal of the American Chemical Society. ,vol. 128, pp. 52- 53 ,(2006) , 10.1021/JA055993L
Ileana Dragutan, Valerian Dragutan, Albert Demonceau, Targeted drugs by olefin metathesis: piperidine-based iminosugars RSC Advances. ,vol. 2, pp. 719- 736 ,(2012) , 10.1039/C1RA00910A
Justin A. M. Lummiss, Nicholas J. Beach, Jeffrey C. Smith, Deryn E. Fogg, Targeting an Achilles heel in olefin metathesis: A strategy for high-yield synthesis of second-generation Grubbs methylidene catalysts Catalysis Science & Technology. ,vol. 2, pp. 1630- 1632 ,(2012) , 10.1039/C2CY20213A