Patents by Inventor Brian M. Stoltz

Brian M. Stoltz has filed for patents to protect the following inventions. This listing includes patent applications that are pending as well as patents that have already been granted by the United States Patent and Trademark Office (USPTO).

  • Publication number: 20170137382
    Abstract: The invention provides heterocyclic compounds with quaternary centers and methods of preparing compounds. Methods include the method for the preparation of a compound of Formula (II): comprising treating a compound of Formula (I): with a transition metal catalyst and under alkylation conditions as valence and stability permit.
    Type: Application
    Filed: December 1, 2016
    Publication date: May 18, 2017
    Inventors: Brian M. Stoltz, Scott C Virgil, David E. White, Taiga Yurino, Yiyang Liu, Douglas C. Behenna, Douglas Duquette, Christian Eidamshaus
  • Publication number: 20170088563
    Abstract: The present invention is directed to a mild, efficient, and general direct C(sp)-H bond silylation. Various embodiments includes methods, each method comprising or consisting essentially of contacting at least one organic substrate comprising a terminal alkynyl C—H bond, with a mixture of at least one organosilane and an alkali metal hydroxide, alkali metal alkoxide, or alkali metal hydride under conditions sufficient to form a silylated terminal alkynyl moiety. The methods are operable in the presence or substantially absence of transition-metal compounds. The systems associated with these methods are also disclosed.
    Type: Application
    Filed: December 12, 2016
    Publication date: March 30, 2017
    Inventors: ANTON TOUTOV, KERRY BETZ, BRIAN M. STOLTZ, WENBO LIU, ROBERT H. GRUBBS
  • Publication number: 20170088562
    Abstract: The present invention describes chemical systems and methods for silylating heteroaromatic organic substrates using at least alkoxide base, preferably a potassium alkoxide base and at least one organodisilane and (b) at least one alkoxide base. Both methods and compositions for affecting these transformations are disclosed.
    Type: Application
    Filed: December 12, 2016
    Publication date: March 30, 2017
    Inventors: ANTON TOUTOV, WENBO LIU, BRIAN M. STOLTZ, ROBERT H. GRUBBS, KERRY BETZ, DAVID P. SCHUMAN
  • Patent number: 9556080
    Abstract: The present invention describes chemical systems and methods for silylating heteroaromatic organic substrates, said system consisting essentially of a mixture of (a) at least one organodisilane and (b) at least alkoxide base, preferably a potassium alkoxide base, and said methods comprising contacting a quantity of the organic substrate with a mixture consisting essentially of (a) at least one organodisilane and (b) at least one alkoxide base, preferably a potassium alkoxide, under conditions sufficient to silylate the heteroaromatic substrate.
    Type: Grant
    Filed: December 17, 2015
    Date of Patent: January 31, 2017
    Assignee: California Institute of Technology
    Inventors: Anton Toutov, Wenbo Liu, Brian M. Stoltz, Robert H. Grubbs, Kerry Betz, David P. Schuman
  • Patent number: 9556206
    Abstract: The present invention is directed to a mild, efficient, and general direct C(sp)-H bond silylation. Various embodiments includes methods, each method comprising or consisting essentially of contacting at least one organic substrate comprising a terminal alkynyl C—H bond, with a mixture of at least one organosilane and an alkali metal hydroxide, under conditions sufficient to form a silylated terminal alkynyl moiety. The methods are operable in the substantially absence of transition-metal compounds. The systems associated with these methods are also disclosed.
    Type: Grant
    Filed: September 1, 2015
    Date of Patent: January 31, 2017
    Assignee: California Institute of Technology
    Inventors: Anton Toutov, Kerry Betz, Brian M. Stoltz, Wenbo Liu, Robert H. Grubbs
  • Patent number: 9518034
    Abstract: This invention provides enantioenriched heterocyclic enaminone compounds with quaternary stereogenic centers and novel methods of preparing the compounds. Methods include the method for the preparation of a compound of formula (I): comprising treating a compound of formula (II): with a transition metal catalyst under alkylation conditions.
    Type: Grant
    Filed: October 14, 2014
    Date of Patent: December 13, 2016
    Assignee: California Institute of Technology
    Inventors: Brian M. Stoltz, Dennis A. Dougherty, Douglas Duquette, Noah Duffy
  • Publication number: 20160347776
    Abstract: The present invention is directed to a mild, efficient, and general direct C(sp2)-H bond silylation of terminal olefins. Various embodiments includes methods, each method comprising or consisting essentially of contacting at least one organic substrate comprising a terminal olefinic C—H bond, with a mixture of at least one organosilane, organosilane, or mixture thereof and an alkali metal alkoxide or alkali metal hydroxide, such that the contacting results in the formation of a silylated olefinic product. The systems associated with these methods are also disclosed.
    Type: Application
    Filed: May 27, 2016
    Publication date: December 1, 2016
    Inventors: ANTON TOUTOV, WENBO LIU, KERRY BETZ, ALEXEY FEDOROV, BRIAN M. STOLTZ, ROBERT H. GRUBBS
  • Publication number: 20160280623
    Abstract: This invention provides efficient and scalable enantioselective methods that yield 2-alkyl-2-allylcycloalkyanone compounds with quaternary stereogenic centers. Methods include the method for the preparation of a compound of formula (I): comprising treating a compound of formula (II) or (III): with a palladium (II) catalyst under alkylation conditions.
    Type: Application
    Filed: March 25, 2016
    Publication date: September 29, 2016
    Inventors: Brian M. Stoltz, Alexander N. Marziale, Robert A. Craig, Douglas Duquette, Kelly E. Kim, Marc Liniger, Yoshitaka Numajiri
  • Patent number: 9440891
    Abstract: The present invention is directed to methods of forming olefins, especially linear alpha olefins from fatty acids or anhydrides, each method comprising: contacting an amount of precursor carboxylic acid anhydride with a palladium catalyst comprising a bidentate bis-phosphine ligand in a reaction mixture so as to form an olefin in a product with the concomittant formation and removal of CO and water from the reaction mixture, either directly or indirectly, wherein the reaction mixture is maintained with a sub-stoichiometric excess of a sacrificial carboxylic acid anhydride, an organic acid, or both, said sub-stoichiometric excess being relative to the amount of the precursor carboxylic acid anhydride. The precursor carboxylic acid anhydride may be added to the reaction mixture directly or formed in situ by the reaction between at least one precursor carboxylic acid with a stoichiometric amount of the sacrificial acid anhydride.
    Type: Grant
    Filed: November 27, 2013
    Date of Patent: September 13, 2016
    Assignee: California Institute of Technology
    Inventors: Yiyang Liu, Brian M. Stoltz, Robert H. Grubbs, Alexey Fedorov, Kelly E. Kim
  • Patent number: 9422259
    Abstract: Compounds represented by Formula I are provided that include synthetic transtaganolide and basiliolide products. Derivatives of these compounds and methods of synthesis are also provided.
    Type: Grant
    Filed: October 31, 2014
    Date of Patent: August 23, 2016
    Assignee: California Institute of Technology
    Inventors: Hosea Nelson, Kei Murakami, Scott C. Virgil, Brian M. Stoltz, Jonathan R. Gordon
  • Publication number: 20160176772
    Abstract: The present invention describes chemical systems and methods for silylating heteroaromatic organic substrates, said system consisting essentially of a mixture of (a) at least one organodisilane and (b) at least alkoxide base, preferably a potassium alkoxide base, and said methods comprising contacting a quantity of the organic substrate with a mixture consisting essentially of (a) at least one organodisilane and (b) at least one alkoxide base, preferably a potassium alkoxide, under conditions sufficient to silylate the heteroaromatic substrate.
    Type: Application
    Filed: December 17, 2015
    Publication date: June 23, 2016
    Inventors: ANTON TOUTOV, WENBO LIU, BRIAN M. STOLTZ, ROBERT H. GRUBBS, KERRY BETZ, DAVID P. SCHUMAN
  • Publication number: 20160176773
    Abstract: This invention provides enantioenriched Mannich adducts with quaternary stereogenic centers and novel methods of preparing the compounds. Methods include the method for the preparation of a compound of formula (I): comprising treating a compound of formula (II): with a transition metal catalyst under alkylation conditions.
    Type: Application
    Filed: December 17, 2015
    Publication date: June 23, 2016
    Inventors: Brian M. Stoltz, Yoshitaka Numajiri, Beau P. Pritchett, Koji Chiyoda
  • Publication number: 20160096810
    Abstract: This invention provides enantioenriched N,O-heterocyclic compounds with quaternary stereogenic centers and novel methods of preparing the compounds. Methods include the method for the preparation of a compound of formula (I): comprising treating a compound of formula (II): with a transition metal catalyst under alkylation conditions.
    Type: Application
    Filed: October 7, 2015
    Publication date: April 7, 2016
    Inventors: Brian M. Stoltz, Yoshitaka Numajiri, Douglas C. Behenna
  • Publication number: 20160060278
    Abstract: The present invention is directed to a mild, efficient, and general direct C(sp)-H bond silylation. Various embodiments includes methods, each method comprising or consisting essentially of contacting at least one organic substrate comprising a terminal alkynyl C—H bond, with a mixture of at least one organosilane and an alkali metal hydroxide, under conditions sufficient to form a silylated terminal alkynyl moiety. The methods are operable in the substantially absence of transition-metal compounds. The systems associated with these methods are also disclosed.
    Type: Application
    Filed: September 1, 2015
    Publication date: March 3, 2016
    Inventors: ANTON TOUTOV, KERRY BETZ, BRIAN M. STOLTZ, WENBO LIU, ROBERT H. GRUBBS
  • Publication number: 20160046653
    Abstract: The present invention describes chemical systems and methods for silylating aromatic organic substrates, said system or method comprising or consisting essentially of a mixture of (a) at least one organosilane and (b) at least one strong base, the definition of strong base now also including hydroxide, especially KOH, said system being preferably, but not necessarily substantially free of a transition-metal compound, and said methods comprising contacting a quantity of the organic substrate with a mixture of (a) at least one organosilane and (b) at least one strong base, under conditions sufficient to silylate the aromatic substrate; wherein said system is substantially free of a transition-metal compound.
    Type: Application
    Filed: August 5, 2015
    Publication date: February 18, 2016
    Inventors: ANTON TOUTOV, KERRY BETZ, ALEXEY FEDEROV, BRIAN M. STOLTZ, WENBO LIU, ROBERT H. GRUBBS
  • Publication number: 20150344392
    Abstract: Insect pheromones and pheromone precursors, containing one or more Z-alkenyl groups, are prepared by treating an alkyne with a copper complex, reducing agent, and proton donor in an organic solvent. The pheromones and pheromone precursors are prepared with high stereoselectivity and substantially no over reduction.
    Type: Application
    Filed: May 29, 2014
    Publication date: December 3, 2015
    Applicant: Suterra, LLC
    Inventors: Eric A. Bercot, Brian M. Stoltz
  • Patent number: 9181164
    Abstract: Insect pheromones and pheromone precursors, containing one or more Z-alkenyl groups, are prepared by treating an alkyne with a copper complex, reducing agent, and proton donor in an organic solvent. The pheromones and pheromone precursors are prepared with high stereoselectivity and substantially no over reduction.
    Type: Grant
    Filed: May 29, 2014
    Date of Patent: November 10, 2015
    Assignee: SUTERRA, LLC
    Inventors: Eric A. Bercot, Brian M. Stoltz
  • Patent number: 9089572
    Abstract: One aspect of the invention relates to compounds that inhibit the activity of p97, such as by binding covalently to a cysteine residue in the active site. In certain embodiments, the invention relates to the treatment of disease, such as cancer, comprising administering a compound of the invention.
    Type: Grant
    Filed: January 20, 2009
    Date of Patent: July 28, 2015
    Assignees: California Institute of Technology, The Scripps Research Institute
    Inventors: Steven J. Brown, Tsui-Fen Chou, Raymond Deshaies, Amanda C. Jones, Hugh Rosen, Brian M. Stoltz
  • Publication number: 20150105552
    Abstract: This invention provides enantioenriched heterocyclic enaminone compounds with quaternary stereogenic centers and novel methods of preparing the compounds. Methods include the method for the preparation of a compound of formula (I): comprising treating a compound of formula (II): with a transition metal catalyst under alkylation conditions.
    Type: Application
    Filed: October 14, 2014
    Publication date: April 16, 2015
    Inventors: Brian M. Stoltz, Dennis A. Dougherty, Douglas Duquette, Noah Duffy
  • Publication number: 20150051411
    Abstract: Compounds represented by Formula I are provided that include synthetic transtaganolide and basiliolide products. Derivatives of these compounds and methods of synthesis are also provided.
    Type: Application
    Filed: October 31, 2014
    Publication date: February 19, 2015
    Applicant: California Institute of Technology
    Inventors: Hosea Nelson, Kei Murakami, Scott C. Virgil, Brian M. Stoltz, Jonathan R. Gordon