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Comparison of Ru- and Mo-Based Chiral Olefin Metathesis Catalysts. Complementarity in Asymmetric Ring-Opening/Cross-Metathesis Reactions of Oxa- and Azabicycles

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G. Alex Cortez,^† Carl A. Baxter,^† Richard R. Schrock,^# and Amir H. Hoveyda*^†

Department of Chemistry, Merkert Chemistry Center, Boston College, Chestnut Hill, Massachusetts 02467, and Department of Chemistry, Massachusetts Institute of Technology, Cambridge, Massachusetts 02139

Org. Lett., 2007, 9 (15), pp 2871–2874

DOI: 10.1021/ol071008h

Publication Date (Web): June 22, 2007

Section:

Heterocyclic Compounds (One Hetero Atom)

Abstract

A comparative study of chiral Mo- and Ru-based catalysts to promote enantioselective synthesis of 2,6-disubstituted pyrans and piperidines through asymmetric ring-opening/cross-metathesis (AROM/CM) reactions is presented. These studies demonstrate the critical complementarity that exists between the two classes of chiral catalysts.

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Citing Articles

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This article has been cited by 16 ACS Journal articles (5 most recent appear below).

Enol Ethers as Substrates for Efficient Z- and Enantioselective Ring-Opening/Cross-Metathesis Reactions Promoted by Stereogenic-at-Mo Complexes: Utility in Chemical Synthesis and Mechanistic Attributes
Miao Yu, Ismail Ibrahem, Masayuki Hasegawa, Richard R. Schrock, and Amir H. Hoveyda
Journal of the American Chemical Society2012 134 (5), 2788-2799
- Enol Ethers as Substrates for Efficient Z- and Enantioselective Ring-Opening/Cross-Metathesis Reactions Promoted by Stereogenic-at-Mo Complexes: Utility in Chemical Synthesis and Mechanistic Attributes
  Miao Yu, Ismail Ibrahem, Masayuki Hasegawa, Richard R. Schrock, and Amir H. Hoveyda
  Journal of the American Chemical Society2012 134 (5), 2788-2799
  The first examples of catalytic enantioselective ring-opening/cross-metathesis (EROCM) reactions that involve enol ethers are reported. Specifically, we demonstrate that catalytic EROCM of several oxa- and azabicycles, cyclobutenes and a cyclopropene with ...
  Abstract | Full Text HTML | Hi-Res PDF | PDF w/ Links
Z-Selective Homodimerization of Terminal Olefins with a Ruthenium Metathesis Catalyst
Benjamin K. Keitz, Koji Endo, Myles B. Herbert, and Robert H. Grubbs
Journal of the American Chemical Society2011 133 (25), 9686-9688
- Z-Selective Homodimerization of Terminal Olefins with a Ruthenium Metathesis Catalyst
  Benjamin K. Keitz, Koji Endo, Myles B. Herbert, and Robert H. Grubbs
  Journal of the American Chemical Society2011 133 (25), 9686-9688
  The cross-metathesis of terminal olefins using a novel ruthenium catalyst results in excellent selectivity for the Z-olefin homodimer. The reaction was found to tolerate a large number of functional groups, solvents, and temperatures while maintaining ...
  Abstract | Full Text HTML | Hi-Res PDF | PDF w/ Links
Chelated Ruthenium Catalysts for Z-Selective Olefin Metathesis
Koji Endo and Robert H. Grubbs
Journal of the American Chemical Society2011 133 (22), 8525-8527
- Chelated Ruthenium Catalysts for Z-Selective Olefin Metathesis
  Koji Endo and Robert H. Grubbs
  Journal of the American Chemical Society2011 133 (22), 8525-8527
  We report the development of ruthenium-based metathesis catalysts with chelating N-heterocyclic carbene (NHC) ligands that catalyze highly Z-selective olefin metathesis. A very simple and convenient procedure for the synthesis of such catalysts has been ...
  Abstract | Full Text HTML | Hi-Res PDF | PDF w/ Links
Reversal of Stereoselectivity in the Cu-Catalyzed Conjugate Addition Reaction of Dialkylzinc to Cyclic Enone in the Presence of a Chiral Azolium Compound
Naoatsu Shibata, Masaki Okamoto, Yuko Yamamoto and Satoshi Sakaguchi
The Journal of Organic Chemistry2010 75 (16), 5707-5715
- Reversal of Stereoselectivity in the Cu-Catalyzed Conjugate Addition Reaction of Dialkylzinc to Cyclic Enone in the Presence of a Chiral Azolium Compound
  Naoatsu Shibata, Masaki Okamoto, Yuko Yamamoto and Satoshi Sakaguchi
  The Journal of Organic Chemistry2010 75 (16), 5707-5715
  Reversal of enantioselectivity in a Cu-catalyzed asymmetric conjugate addition reaction of dialkylzinc to cyclic enone with use of the same chiral ligand was successfully achieved. The reaction of 2-cyclohexen-1-one (30) with Et2Zn catalyzed by Cu(OTf)2 ...
  Abstract | Full Text HTML | Hi-Res PDF | PDF w/ Links
Ruthenium-Based Heterocyclic Carbene-Coordinated Olefin Metathesis Catalysts
Georgios C. Vougioukalakis and Robert H. Grubbs
Chemical Reviews2010 110 (3), 1746-1787
- Ruthenium-Based Heterocyclic Carbene-Coordinated Olefin Metathesis Catalysts
  Georgios C. Vougioukalakis and Robert H. Grubbs
  Chemical Reviews2010 110 (3), 1746-1787
  Abstract | Full Text HTML | Hi-Res PDF | PDF w/ Links