Title:
GROUP 8 TRANSITION METAL CARBENE COMPLEXES AS ENANTIOSELECTIVE OLEFIN METATHESIS CATALYSTS
Document Type and Number:
WIPO Patent Application WO2002083742
Kind Code:
A3
Abstract:
The invention pertains to the preparation and use of Group 8 transition metal carbene compounds as catalysts for olefin cross- metathesis reactions, and for enantioselective reactions in particular. The synthesis of these compounds and details of their use as catalysts is also provided. The carbene compounds are further ligated by a five-membered heterocycle ligand sigma bonded to the metal atom. This ligand has two nitrogen, phosphorus, oxygen or sulfur heteroatoms in the ring adjacent to the carbon atom bonded to the metal atom. This ligand is saturated, the two heteroatoms are preferably nitrogen with phenyl groups bonded to them, and the other two distal carbon atoms of the ligand are preferably chiral.
Inventors:
GRUBBS ROBERT H (US)
WARD DONALD W (US)
SEIDERS THOMAS J (US)
GOLDBERG STEVEN D (US)
WARD DONALD W (US)
SEIDERS THOMAS J (US)
GOLDBERG STEVEN D (US)
Application Number:
PCT/US2002/012165
Publication Date:
December 19, 2002
Filing Date:
April 16, 2002
Export Citation:
Assignee:
CALIFORNIA INST OF TECHN (US)
GRUBBS ROBERT H (US)
WARD DONALD W (US)
SEIDERS THOMAS J (US)
GOLDBERG STEVEN D (US)
GRUBBS ROBERT H (US)
WARD DONALD W (US)
SEIDERS THOMAS J (US)
GOLDBERG STEVEN D (US)
International Classes:
C07F15/00; C08F4/06; C08F4/80; (IPC1-7): C08F4/06; C08F4/80; C07F9/70; C07F9/90; C07F9/94; C07F15/00; C07F17/02; C07F15/02; C07F15/04; C07F15/06
Domestic Patent References:
| WO2000015339A1 | 2000-03-23 |
Foreign References:
| US6409875B1 | 2002-06-25 | |||
| US6426419B1 | 2002-07-30 | |||
| US6291616B1 | 2001-09-18 | |||
| US6271315B1 | 2001-08-07 | |||
| US20010006988A1 | 2001-07-05 | |||
| US20010049398A1 | 2001-12-06 | |||
| US20020022741A1 | 2002-02-21 | |||
| US20020107138A1 | 2002-08-08 | |||
| JP2001270892A | 2001-10-02 | |||
| US6107420A | 2000-08-22 | |||
| EP0798041A1 | 1997-10-01 | |||
| DE4447066A1 | 1996-07-04 |
Other References:
TRNKA T.M. ET AL.: "The development of L2X2 mu-chr olefin metathesis catalysts: an organometallic success story", ACC. CHEM. RES., vol. 34, no. 1, 2001, pages 18 - 29, XP002951799
SEIDERS T.J. ET AL., ORG. LETT., vol. 3, no. 20, 2001, pages 3225 - 3228, XP002220700
TRNKA T.M. ET AL., ORGANOMETALLICS, vol. 20, no. 18, 2001, pages 3845 - 3847, XP001093392
SANFORD M.S. ET AL., J. AM. CHEM. SOC., vol. 123, no. 4, 2001, pages 749 - 750, XP002957484
SANFORD M.S. ET AL., J. AM. CHEM. SOC., vol. 123, no. 27, 2001, pages 6543 - 6554, XP002957485
BUCHMEISER M.R., CHEM. REV., vol. 100, no. 4, 2000, pages 1565 - 1604, XP002957486
WESKAMP T. ET AL., ANGEW. CHEM. INT. ED. ENG., vol. 37, no. 18, 1998, pages 2490 - 2493, XP002951798
FURSTNER A., ANGEW. CHEM. INT. ED. ENG., vol. 39, 2000, pages 3012 - 3043, XP002957487
HUANG J. ET AL., J. AM. CHEM. SOC., vol. 121, no. 12, 1999, pages 2674 - 2678, XP002928348
JAFARPOUR L. ET AL., ORGANOMETALLICS, vol. 19, no. 11, 2000, pages 2055 - 2057, XP002957488
SCHOLL M. ET AL., TETRAHEDRON LETTERS, vol. 40, 1999, pages 2247 - 2250, XP004157444
SCHOLL M. ET AL., ORG. LETT., vol. 1, no. 6, 1999, pages 953 - 956, XP000984756
ULMAN M. ET AL., J. ORG. CHEM., vol. 64, no. 19, 1999, pages 7202 - 7207, XP001037574
BOURISSOU D. ET AL., CHEM. REV., vol. 100, no. 1, 2000, pages 39 - 91, XP001037594
SEIDERS T.J. ET AL., ORG. LETT., vol. 3, no. 20, 2001, pages 3225 - 3228, XP002220700
TRNKA T.M. ET AL., ORGANOMETALLICS, vol. 20, no. 18, 2001, pages 3845 - 3847, XP001093392
SANFORD M.S. ET AL., J. AM. CHEM. SOC., vol. 123, no. 4, 2001, pages 749 - 750, XP002957484
SANFORD M.S. ET AL., J. AM. CHEM. SOC., vol. 123, no. 27, 2001, pages 6543 - 6554, XP002957485
BUCHMEISER M.R., CHEM. REV., vol. 100, no. 4, 2000, pages 1565 - 1604, XP002957486
WESKAMP T. ET AL., ANGEW. CHEM. INT. ED. ENG., vol. 37, no. 18, 1998, pages 2490 - 2493, XP002951798
FURSTNER A., ANGEW. CHEM. INT. ED. ENG., vol. 39, 2000, pages 3012 - 3043, XP002957487
HUANG J. ET AL., J. AM. CHEM. SOC., vol. 121, no. 12, 1999, pages 2674 - 2678, XP002928348
JAFARPOUR L. ET AL., ORGANOMETALLICS, vol. 19, no. 11, 2000, pages 2055 - 2057, XP002957488
SCHOLL M. ET AL., TETRAHEDRON LETTERS, vol. 40, 1999, pages 2247 - 2250, XP004157444
SCHOLL M. ET AL., ORG. LETT., vol. 1, no. 6, 1999, pages 953 - 956, XP000984756
ULMAN M. ET AL., J. ORG. CHEM., vol. 64, no. 19, 1999, pages 7202 - 7207, XP001037574
BOURISSOU D. ET AL., CHEM. REV., vol. 100, no. 1, 2000, pages 39 - 91, XP001037594
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