Catalytic Enantioselective Olefin Metathesis in Natural Product Synthesis. Chiral Metal‐Based Complexes that Deliver High Enantioselectivity and More
- 22 December 2009
- journal article
- review article
- Published by Wiley in Angewandte Chemie-International Edition
- Vol. 49 (1), 34-44
- https://doi.org/10.1002/anie.200904491
Abstract
Chiral olefin metathesis catalysts enable chemists to access enantiomerically enriched small molecules with high efficiency; synthesis schemes involving such complexes can be substantially more concise than those that would involve enantiomerically pure substrates and achiral Mo alkylidenes or Ru‐based carbenes. The scope of research towards design and development of chiral catalysts is not limited to discovery of complexes that are merely the chiral versions of the related achiral variants. A chiral olefin metathesis catalyst, in addition to furnishing products of high enantiomeric purity, can offer levels of efficiency, product selectivity and/or olefin stereoselectivity that are unavailable through the achiral variants. Such positive attributes of chiral catalysts (whether utilized in racemic or enantiomerically enriched form) should be considered as general, applicable to other classes of transformations.Keywords
This publication has 89 references indexed in Scilit:
- Highly Z-Selective Metathesis Homocoupling of Terminal OlefinsJournal of the American Chemical Society, 2009
- The Significance of Degenerate Processes to Enantioselective Olefin Metathesis Reactions Promoted by Stereogenic-at-Mo ComplexesJournal of the American Chemical Society, 2009
- Endo-Selective Enyne Ring-Closing Metathesis Promoted by Stereogenic-at-Mo Monoalkoxide and Monoaryloxide Complexes. Efficient Synthesis of Cyclic Dienes Not Accessible through Reactions with Ru CarbenesJournal of the American Chemical Society, 2009
- Z-Selective Olefin Metathesis Processes Catalyzed by a Molybdenum Hexaisopropylterphenoxide Monopyrrolide ComplexJournal of the American Chemical Society, 2009
- Highly Z- and Enantioselective Ring-Opening/Cross-Metathesis Reactions Catalyzed by Stereogenic-at-Mo Adamantylimido ComplexesJournal of the American Chemical Society, 2009
- Efficient Boron−Copper Additions to Aryl-Substituted Alkenes Promoted by NHC−Based Catalysts. Enantioselective Cu-Catalyzed Hydroboration ReactionsJournal of the American Chemical Society, 2009
- Design and Stereoselective Preparation of a New Class of Chiral Olefin Metathesis Catalysts and Application to Enantioselective Synthesis of Quebrachamine: Catalyst Development Inspired by Natural Product SynthesisJournal of the American Chemical Society, 2008
- Highly efficient molybdenum-based catalysts for enantioselective alkene metathesisNature, 2008
- Enantioselective Synthesis of All‐Carbon Quaternary Stereogenic Centers by Catalytic Asymmetric Conjugate Additions of Alkyl and Aryl Aluminum Reagents to Five‐, Six‐, and Seven‐Membered‐Ring β‐Substituted Cyclic EnonesAngewandte Chemie-International Edition, 2008
- Highly Reactive, General and Long-Lived Catalysts for Palladium-Catalyzed Amination of Heteroaryl and Aryl Chlorides, Bromides, and Iodides: Scope and Structure–Activity RelationshipsJournal of the American Chemical Society, 2008