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).

  • Patent number: 10343996
    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: Grant
    Filed: July 30, 2018
    Date of Patent: July 9, 2019
    Assignee: California Institute of Technology
    Inventors: Brian M. Stoltz, Scott C. Virgil, David E. White, Taiga Yurino, Yiyang Liu, Douglas C. Behenna, Douglas Duquette, Christian Eidamshaus
  • Patent number: 10336678
    Abstract: The present disclosure provides methods for enantioselective synthesis of acyclic ?-quaternary carboxylic acid derivatives via iridium-catalyzed allylic alkylation.
    Type: Grant
    Filed: May 11, 2018
    Date of Patent: July 2, 2019
    Assignee: California Institute of Technology
    Inventors: Samantha E. Shockley, John C. Hethcox, Brian M. Stoltz
  • Publication number: 20190135754
    Abstract: The present disclosure provides methods for enantioselective synthesis of cyclic and acyclic ?-quaternary carboxylic acid derivatives via nickel-catalyzed allylic alkylation.
    Type: Application
    Filed: November 1, 2018
    Publication date: May 9, 2019
    Inventors: Brian M. Stoltz, Aurapat Ngamnithiporn, Carina I. Jette, Shoshana Bachman, Scott C. Virgil, Sebastian Lackner
  • Publication number: 20190077796
    Abstract: This disclosure provides methods for intermolecular enantioselective C-acylation of lactams with quaternary stereogenic centers by applying a chiral Ni catalyst. The methods comprise treating a lactam with a chiral Ni catalyst, an aryl nitrile, and an aryl halide.
    Type: Application
    Filed: August 6, 2018
    Publication date: March 14, 2019
    Inventors: Brian M. Stoltz, Masaki Hayashi, Satoshi Hashimoto
  • Publication number: 20190055182
    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: October 22, 2018
    Publication date: February 21, 2019
    Inventors: Brian M. Stoltz, Alexander N. Marziale, Robert A. Craig, Douglas Duquette, Kelly E. Kim, Marc Liniger, Yoshitaka Numajiri
  • Publication number: 20190048009
    Abstract: (?)-Jorumycin, ecteinascidin 743, saframycin A and related compounds, methods of preparing the same, formulations comprising the compounds, and methods of treating proliferative diseases with the same are provided.
    Type: Application
    Filed: July 18, 2018
    Publication date: February 14, 2019
    Inventors: Brian M. Stoltz, Eric R. Welin, Scott C. Virgil, Pamela Tadross, Gerit Maria Pototschnig, Aurapat (Fa) Ngamnithiporn, Kenji Negoro, Guillaume Lapointe, Max Klatte, Christopher Haley, Christian Gruenanger, Emil Glibstrup, Christopher Gilmore, Kevin McCormack Allan
  • Publication number: 20190048030
    Abstract: The present disclosure describes novel silylated heteroaromatic derivatives, including those prepared by methods comprising the use of hydrosilanes and at least one strong base, the definition of strong base now also including hydroxide, especially KOH.
    Type: Application
    Filed: October 12, 2018
    Publication date: February 14, 2019
    Inventors: Anton Toutov, Kerry Betz, Alexey Fedorov, Brian M. Stoltz, Wenbo Liu, Robert H. Grubbs
  • Publication number: 20180339968
    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: July 30, 2018
    Publication date: November 29, 2018
    Inventors: Brian M. Stoltz, Scott C. Virgil, David E. White, Taiga Yurino, Yiyang Liu, Douglas C. Behenna, Douglas Duquette, Christian Eidamshaus
  • Publication number: 20180327343
    Abstract: The present disclosure provides methods for enantioselective synthesis of acyclic ?-quaternary carboxylic acid derivatives via iridium-catalyzed allylic alkylation.
    Type: Application
    Filed: May 11, 2018
    Publication date: November 15, 2018
    Inventors: Samantha E. Shockley, John C. Hethcox, Brian M. Stoltz
  • Patent number: 10125153
    Abstract: The present invention describes chemical systems and methods for silylating N—H bonds of aliphatic amines, said system or method comprising or consisting essentially of a mixture of (a) at least one organosilane and (b) at least one 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 replace an N—H bond with a silyl N—Si bond.
    Type: Grant
    Filed: November 6, 2017
    Date of Patent: November 13, 2018
    Assignee: California Institute of Technology
    Inventors: Anton Toutov, Kerry Betz, Alexey Fedorov, Brian M. Stoltz, Wenbo Liu, Robert H. Grubbs
  • Patent number: 10106479
    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: Grant
    Filed: March 25, 2016
    Date of Patent: October 23, 2018
    Assignee: California Institute of Technology
    Inventors: Brian M. Stoltz, Alexander N. Marziale, Robert A. Craig, Douglas Duquette, Kelly E. Kim, Marc Liniger, Yoshitaka Numajiri
  • Patent number: 10072030
    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: Grant
    Filed: December 12, 2016
    Date of Patent: September 11, 2018
    Assignee: California Institute of Technology
    Inventors: Anton Toutov, Kerry Betz, Brian M. Stoltz, Wenbo Liu, Robert H. Grubbs
  • Patent number: 10059726
    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: Grant
    Filed: May 27, 2016
    Date of Patent: August 28, 2018
    Assignee: California Institute of Technology
    Inventors: Anton Toutov, Wenbo Liu, Kerry Betz, Alexey Fedorov, Brian M. Stoltz, Robert H. Grubbs
  • Patent number: 10040784
    Abstract: This disclosure provides methods for intermolecular enantioselective C-acylation of lactams with quaternary stereogenic centers by applying a chiral Ni catalyst. The methods comprise treating a lactam with a chiral Ni catalyst, an aryl nitrile, and an aryl halide.
    Type: Grant
    Filed: March 9, 2017
    Date of Patent: August 7, 2018
    Assignee: California Institute of Technology
    Inventors: Brian M. Stoltz, Masaki Hayashi, Satoshi Hashimoto
  • Patent number: 10035769
    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: Grant
    Filed: December 1, 2016
    Date of Patent: July 31, 2018
    Assignee: California Institute of Technology
    Inventors: Brian M. Stoltz, Scott C. Virgil, David E. White, Taiga Yurino, Yiyang Liu, Douglas C. Behenna, Douglas Duquette, Christian Eidamshaus
  • Publication number: 20180057514
    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.
    Type: Application
    Filed: November 6, 2017
    Publication date: March 1, 2018
    Inventors: ANTON TOUTOV, KERRY BETZ, ALEXEY FEDOROV, BRIAN M. STOLTZ, WENBO LIU, ROBERT H. GRUBBS
  • Patent number: 9809607
    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 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.
    Type: Grant
    Filed: August 5, 2015
    Date of Patent: November 7, 2017
    Assignee: California Institute of Technology
    Inventors: Anton Toutov, Kerry Betz, Alexey Fedorov, Brian M. Stoltz, Wenbo Liu, Robert H. Grubbs
  • Patent number: 9764995
    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: Grant
    Filed: December 12, 2016
    Date of Patent: September 19, 2017
    Assignee: California Institute of Technology
    Inventors: Anton Toutov, Wenbo Liu, Brian M. Stoltz, Robert H. Grubbs, Kerry Betz, David P. Schuman
  • Publication number: 20170260172
    Abstract: This disclosure provides methods for intermolecular enantioselective C-acylation of lactams with quaternary stereogenic centers by applying a chiral Ni catalyst. The methods comprise treating a lactam with a chiral Ni catalyst, an aryl nitrile, and an aryl halide.
    Type: Application
    Filed: March 9, 2017
    Publication date: September 14, 2017
    Inventors: Brian M. Stoltz, Masaki Hayashi, Satoshi Hashimoto
  • Publication number: 20170240571
    Abstract: The present invention is directed to compositions for silylating organic substrates containing C—H or O—H bonds, especially heteroaromatic substrates. The compositions are derived from the preconditioning of mixtures of hydrosilanes or organodisilanes with bases, including metal hydroxide and metal alkoxide bases. In some embodiments, the preconditioning results in the formation of reactive silicon hydride species.
    Type: Application
    Filed: February 22, 2017
    Publication date: August 24, 2017
    Inventors: ANTON TOUTOV, WENBO LIU, DAVID P. SCHUMAN, BRIAN M. STOLTZ, ROBERT H. GRUBBS H. GRUBBS