The Trustees of Boston College

Massachusetts Institute of Technology

Amir H Hoveyda

Richard Royce Schrock

Jason Kingsbury

Steven Garber

John T Fourkas

Margaret M Flook

Ming Joo Koh

Yu Zhao

Simon J Meek

Annie J King

Brian Lawrence Gray

Miao Yu

Chenbo Wang

Steven J Malcolmson

Sebastian Torker

Thach T Nguyen

Dmitry Vyacheslavovich Peryshkov

Chaofan Xu

Daniel T Robbins

Hanmo Zhang

Tatiana Pilyugina

R Kashif M Khan

Daniel L Silverio

Robert V O'Brien

Josep Llaveria Cros

Elizabeth T Kiesewetter

Smaranda C Marinescu

Joshua Van Veldhuizen

Xiao Shen

Jakub Hyvl

Malte Sebastian Mikus

Robert V O' Brien

Steven B Garber

Jason S Kingsbury

Richard R Schrock

Method of making a cross metathesis product, the method comprising at least step (X) or step (Y): (X) reacting in a cross metathesis reaction a first compound comprising a terminal olefinic group with a second compound comprising a terminal olefinic group, wherein the first and the second compound may be identical or may be different from one another; or (Y) reacting in a ring-closing metathesis reaction two terminal olefinic groups which are comprised in a third compound; wherein the reacting in step (X) or step (Y) is performed in the presence of a ruthenium carbene complex comprising a [Ru&#x2550;C]-moiety and an internal olefin.

Method of making a cross metathesis product

Method of forming a trisubstituted ethylene compound, the method comprising: (A) providing a trisubstituted ethylene compound bearing a first, a second and a third substituent, in which the first and the second substituent are bound to the one olefinic carbon atom and are different from one another; (B) providing a monosubstituted ethylene compound or a disubstituted ethylene compound in which the substituents are vicinally bound to the olefinic carbon atoms, bearing at least a fourth substituent, respectively; (C) subjecting the trisubstituted ethylene compound provided in step (A) to a cross-metathesis reaction with olefin provided in step (B) to form said trisubstituted ethylene, wherein the cross-metathesis reaction is catalysed by a transition metal complex bearing ligands from which one ligand is a carbene ligand, wherein the carbene complex is characterized by a M=C moiety, wherein M is the transition metal; and wherein the reaction proceeds stereoselectively.

Method of preparing trisubstituted ethylene compounds

The present disclosure provides compounds, compositions, and methods for preparing alkenyl halides and/or haloalkyl-substituted olefins with Z-selectivity. The methods are particularly useful for preparing alkenyl fluorides such as CF-substituted olefins by means of cross-metathesis reactions using halogen-containing molybdenum and tungsten complexes.

Halogen-containing metathesis catalysts and methods thereof

Highly active, recoverable and recyclable transition metal-based metathesis catalysts and their organometallic complexes including dendrimeric complexes are disclosed, including a Ru complex bearing a 1,3-dimesityl-4,5-dihydroimidazol-2-ylidene and styrenyl ether ligand. The heterocyclic ligand significantly enhances the catalytic activity, and the styrenyl ether allows for the easy recovery of the Ru complex. Derivatized catalysts capable of being immobilized on substrate surfaces are also disclosed. The present catalysts can be used to catalyze ring-closing metathesis (RCM), ring-opening (ROM) and cross metatheses (CM) reactions, and promote the efficient formation of various trisubstituted olefins at ambient temperature in high yield.

Recyclable metathesis catalysts

The present invention provides compositions comprising metal complexes, and related methods. In some embodiments, metal complexes of the invention may be useful as catalysts for chemical reactions, including metathesis reactions, wherein the catalysts exhibit enhanced activity and stereoselectivity. In some embodiments, the invention may advantageously provide metal complexes comprising a stereogenic metal atom. Such metal complexes may be useful in enantioselective catalysis.

Catalysts for metathesis reactions including enantioselective olefin metathesis, and related methods

The present invention relates generally to catalysts and processes for the Z-selective formation of internal olefin(s) from terminal olefin(s) via homo-metathesis reactions.

Highly Z-selective olefin metathesis

The present application provides, among other things, compounds and methods for metathesis reactions. In some embodiments, provided compounds promote highly efficient and highly Z-selective metathesis. In some embodiments, provided compounds and methods are particularly useful for producing allyl alcohols. In some embodiments, provided compounds have the structure of formula I. In some embodiments, provided compounds comprise ruthenium, and a ligand bonded to ruthenium through a sulfur atom.

Catalysts for efficient Z-selective metathesis

The present application provides, among other things, compounds and methods for metathesis reactions. In some embodiments, the present disclosure provides methods for preparing alkenyl halide with regioselectivity and/or stereoselectivity. In some embodiments, the present disclosure provides methods for preparing alkenyl halide with regioselectivity and Z-selectivity. In some embodiments, the present disclosure provides methods for preparing alkenyl halide with regioselectivity and E-selectivity. In some embodiments, provided technologies are particularly useful for preparing alkenyl fluorides. In some embodiments, a provided compound useful for metathesis reactions has the structure of formula II-a. In some embodiments, a provided compound useful for metathesis reactions has the structure of formula II-b.

Metathesis catalysts and methods thereof

The present invention relates generally to olefin metathesis. In some embodiments, the present invention provides methods for Z-selective ring-closing metathesis.

Z-selective ring-closing metathesis reactions

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The current application describes tungsten oxo alkylidene complexes for olefin metathesis.

The present invention provides organic molecules and methods thereof for reactions between organoboron reagents and double bonds, such as imines or carbonyls, to stereoselectively provide chiral products including amines and alcohols, entities useful for the preparation of biologically active molecules.

Simple organic molecules as catalysts for practical and efficient enantioselective synthesis of amines and alcohols

Growing community of inventors

Lincoln, MA, United States of America

Amir H Hoveyda