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Z-Selective Cross-Metathesis and Homodimerization of …

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Kinetically controlled E-selective catalytic olefin metathesis

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Kinetically controlled E-selective catalytic olefin metathesis.

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Research into the structure and stability of metallacyclobutane intermediates has led to the proposal of models to impart Z-selectivity in metathesis reactions. Having the ability to influence the orientation of metallacyclobutane substituents to cause productive formation of Z- double bonds using steric and electronic effects was highly desired. The first successful realization of this concept was by Schrock and Hoveyda et al. who synthesized monoaryloxide pyrolidine (MAP) complexes of tungsten and molybdenum that promoted Z-selective CM. The Z-selectivity of these catalysts was attributed to the difference in the size of the two axial ligands. This size difference influences the orientation of the substituents on the forming/incipient metallacyclobutane intermediate to a cis-geometry and leads to productive formation of Z-olefins. These catalysts have shown great utility in the synthesis of complicated natural product precursors and stereoregular polymers. More recently, ruthenium catalysts capable of promoting Z-selective metathesis have been reported by our group and others. This thesis will discuss the development of ruthenium-based NHC chelated Z-selective catalysts, studies probing their unique metathesis mechanism, and synthetic applications that have been investigated thus far.

Publications about olefin metathesis will generally discuss how the discovery and development of well-defined catalysts to carry out this unique transformation have revolutionized many fields, from natural product and materials chemistry, to green chemistry and biology. However, until recently, an entire manifestation of this methodology had been inaccessible. Except for a few select examples, metathesis catalysts favor the thermodynamic trans- or E-olefin products in cross metathesis (CM), macrocyclic ring closing metathesis (mRCM), ring opening metathesis polymerization (ROMP), and many other types of reactions. Judicious choice of substrates had allowed for the direct synthesis of cis- or Z-olefins or species that could be converted upon further reaction, however the catalyst controlled synthesis of Z-olefins was not possible until very recently.

Z-Selective Olefin Metathesis Reactions - XiMo: …
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Z-selective Cross-Metathesis of Allylic Amides

Olefin cross-metathesis (CM) is a thermodynamically controlled metathesis reaction that is governed by statistical product distributions and a mixture of olefin stereoisomers. In fact, while the reaction allows for the functionalization of alpha-olefins under mild conditions, it has not been used widely due to a lack of selective processes. The research effort disclosed here has provided some new solutions to the selectivity issues involved with CM. These including the use of olefins with altered steric and electronic properties allowing for selective olefin functionalization by CM. After an introduction to state-of-the-art CM in Chapter 1, the discussion continues with CM work in earlier generation ruthenium catalyst systems (Chapter 2). The next two chapters reveal new substrate scope in CM using more active ruthenium based catalysts developed in this group, including the synthesis of trisubstituted olefins (Chapter 3) and directly functionalized olefins (Chapter 4). Once discoveries in expanding substrate scope were accomplished, the final chapter outlines an empirical model for understanding the electronic and steric factors in CM selectivity across a variety of olefin metathesis catalysts. This model provides a method to determine if selective CM can be performed for target-oriented synthetic efforts. In addition, a better understanding of selectivity issues allows for the discovery of new reaction platforms and expands the synthetic utility of CM. These are discussed in Chapter 5 and describe CM as a method to install structural elements as well as to synthesize reagents for subsequent transformation.

Z-Selective Catalytic Olefin Cross-Metathesis Nature ..

“Enantioselective Total Synthesis of Clavirolide C. Applications of Cu-Catalyzed Asymmetric Conjugate Additions and Ru-Catalyzed Ring-Closing Metathesis,” M. Kevin Brown and Amir H. Hoveyda, .

Z-Selective Olefin Metathesis Reactions.

Hyperbranched Aliphatic Polyester via Cross-Metathesis Polymerization: Synthesis and Postpolymerization ModificationFu-Rong Zeng, Ji-Mei Ma, Lin-Hao Sun, Zhen Zeng, Hong Jiang,* and Zi-Long Li*Macromol Rapid Commun 2017 ASAPCopper …

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