公开(公告)号：US09701704B2

公开(公告)日：2017-07-11

申请号：US15074545

申请日：2016-03-18

Applicant: CALIFORNIA INSTITUTE OF TECHNOLOGY

Inventor： Choon Woo Lee ,  Robert H. Grubbs ,  Pablo E. Guzman ,  Tonia S. Ahmed ,  T. Patrick Montgomery

IPC: C07F15/00 ,  B01J31/28 ,  C07C67/30 ,  C07D313/00 ,  C07C67/475 ,  B01J31/12

CPC classification number: C07F15/0046 ,  B01J31/122 ,  B01J31/28 ,  B01J2231/543 ,  B01J2531/821 ,  C07B2200/09 ,  C07C67/293 ,  C07C67/30 ,  C07C67/333 ,  C07C67/475 ,  C07C2601/10 ,  C07D313/00 ,  C08F2500/25 ,  C08G61/08 ,  C08G2261/3322 ,  C08G2261/418 ,  C07C69/74 ,  C07C69/16 ,  C07C69/78 ,  C07C69/76

Abstract: This invention relates generally to olefin metathesis catalyst compounds, to the preparation of such compounds, and the use of such catalysts in the metathesis of olefins and olefin compounds, more particularly, in the use of such catalysts in (E)-selective olefin metathesis reactions. The invention has utility in the fields of catalysis, organic synthesis, polymer chemistry, and industrial and fine chemicals chemistry.

公开(公告)号：US11866398B2

公开(公告)日：2024-01-09

申请号：US17055970

申请日：2019-05-14

Applicant: California Institute of Technology

Inventor： Jiaming Li ,  Xu Chen ,  Tonia S. Ahmed ,  Brian M. Stoltz ,  Robert H. Grubbs

IPC: C07C405/00 ,  B01J23/46

CPC classification number: C07C405/0016 ,  B01J23/462 ,  C07C2601/10

Abstract: This invention relates generally to the synthesis of Δ12-Prostaglandin J product using stereoretentive ruthenium olefin metathesis catalysts supported by dithiolate ligands. Δ12-Prostaglandin J products were generated with excellent selectivity (>99% Z) and in moderate to high/good yields (47% to 80% yield; 58% to 80% yield).

公开(公告)号：US11807617B2

公开(公告)日：2023-11-07

申请号：US17336756

申请日：2021-06-02

Applicant: CALIFORNIA INSTITUTE OF TECHNOLOGY

Inventor： Tonia S. Ahmed ,  Robert H. Grubbs

IPC: C07D313/00 ,  B01J31/22

CPC classification number: C07D313/00 ,  B01J31/226 ,  B01J31/2273 ,  B01J31/2291 ,  B01J2231/543 ,  B01J2531/821

Abstract: A highly efficient, Z-selective ring-closing metathesis system for the formation of macrocycles using a stereoretentive, ruthenium-based catalyst supported by a dithiolate ligand is reported. This catalyst is demonstrated to be remarkably active as observed in initiation experiments showing complete catalyst initiation at −20° C. within 10 min. Using easily accessible diene starting materials bearing a Z-olefin moiety, macrocyclization reactions generated products with significantly higher Z-selectivity in appreciably shorter reaction times, in higher yield, and with much lower catalyst loadings than in previously reported systems. Macrocyclic lactones ranging in size from twelve-membered to seventeen-membered rings are synthesized in moderate to high yields (68-79% yield) with excellent Z-selectivity (95%-99% Z).

公开(公告)号：US11407726B2

公开(公告)日：2022-08-09

申请号：US16770153

申请日：2018-12-04

Applicant: California Institute of Technology

Inventor： Tonia S. Ahmed ,  T. Patrick Montgomery ,  Robert H. Grubbs

IPC: C07D313/00 ,  B01J31/22

Abstract: This invention relates generally to the synthesis of E-macrocycles using stereoretentive ruthenium olefin metathesis catalysts supported by dithioiate ligands. Macrocycles were generated with excellent selectivity (>99% E) and in moderate to high/good yields (47% to 80% yield; 58% to 80% yield) from diene starting materials bearing two E-olefins or bearing one E-olefin and one terminal olefin, A variety of rings were constructed, ranging from 12- to 18-membered macrocycles, including the antibiotic recifeiolide. The invention has utility in the fields of organometallics and organic synthesis.

公开(公告)号：US10857530B2

公开(公告)日：2020-12-08

申请号：US16060466

申请日：2016-12-09

Applicant: Umicore AG & Co. KG ,  California Institute of Technology

Inventor： Adam M. Johns ,  T. Patrick Montgomery ,  Tonia S. Ahmed ,  Robert H. Grubbs ,  Richard L. Pederson

IPC: B01J31/22 ,  C07C6/06 ,  C07C6/04

Abstract: This invention relates generally to metathesis catalysts and the use of such catalysts in the metathesis of olefins and olefin compounds, more particularly, in the use of such catalysts in Z and E selective olefin metathesis reactions. The invention has utility in the fields of organometallics and organic synthesis.

公开(公告)号：US11053209B2

公开(公告)日：2021-07-06

申请号：US16611329

申请日：2018-04-24

Applicant: CALIFORNIA INSTITUTE OF TECHNOLOGY

Inventor： Tonia S. Ahmed ,  Robert H. Grubbs

IPC: C07D313/00 ,  B01J31/22

Abstract: A highly efficient, Z-selective ring-closing metathesis system for the formation of macrocycles using a stereoretentive, ruthenium-based catalyst supported by a dithiolate ligand is reported. This catalyst is demonstrated to be remarkably active as observed in initiation experiments showing complete catalyst initiation at −20° C. within 10 min. Using easily accessible diene starting materials bearing a Z-olefin moiety, macrocyclization reactions generated products with significantly higher Z-selectivity in appreciably shorter reaction times, in higher yield, and with much lower catalyst loadings than in previously reported systems. Macrocyclic lactones ranging in size from twelve-membered to seventeen-membered rings are synthesized in moderate to high yields (68-79% yield) with excellent Z-selectivity (95%-99% Z).

公开(公告)号：US20210017111A1

公开(公告)日：2021-01-21

申请号：US16922290

申请日：2020-07-07

Applicant: California Institute of Technology

Inventor： Jiaming Li ,  Chen Xu ,  Tonia S. Ahmed ,  Robert H. Grubbs ,  Brian M. Stoltz

IPC: C07C45/29 ,  C07C49/577 ,  C07C49/557

Abstract: The present disclosure is directed to methods of preparing prostaglandin J natural products by stereoretentive metatheses reactions and intermediates used in the synthesis of these natural products, including the use of intermediates of Formula (I-A), where R1 is defined in the specification