Endo-selective enyne ring-closing metathesis promoted by stereogenic-at-W mono-pyrrolide complexes

Organic Letters

Volumn 13, Issue 4, 2011, Pages 784-787

  Zhao, Yu ^a   Hoveyda, Amir H ^b   Schrock, Richard R ^a  

^a BOSTON COLLEGE   (United States)

^b MASSACHUSETTS INSTITUTE OF TECHNOLOGY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ALKENE; ALKYNE; MOLYBDENUM; ORGANOMETALLIC COMPOUND; PYRROLE DERIVATIVE; TUNGSTEN;

ARTICLE; CHEMICAL STRUCTURE; CHEMISTRY; COMBINATORIAL CHEMISTRY; CYCLIZATION; STEREOISOMERISM; SYNTHESIS;

ALKENES; ALKYNES; COMBINATORIAL CHEMISTRY TECHNIQUES; CYCLIZATION; MOLECULAR STRUCTURE; MOLYBDENUM; ORGANOMETALLIC COMPOUNDS; PYRROLES; STEREOISOMERISM; TUNGSTEN;

EID: 79951602333     PISSN: 15237060     EISSN: 15237052     Source Type: Journal    
DOI: 10.1021/ol1030525     Document Type: Article

References (19)

1. Schaverien, C. J.; Dewan, J. C.; Schrock, R. R. J. Am. Chem. Soc. 1986, 108, 2771-2773
2. Schrock, R. R. Chem. Rev. 2002, 102, 145-180
3. Schrock, R. R.; Hoveyda, A. H. Angew. Chem., Int. Ed. 2003, 42, 4592-4633
4. Schrock, R. R. Chem. Rev. 2009, 109, 3211-3226
5. Enantioselective RCM: Malcolmson, S. J.; Meek, S. J.; Sattely, E. S.; Schrock, R. R.; Hoveyda, A. H. Nature 2008, 456, 933-937
6. Sattely, E. S.; Meek, S. J.; Malcolmson, S. J.; Schrock, R. R.; Hoveyda, A. H. J. Am. Chem. Soc. 2009, 131, 943-953
7. Meek, S. J.; Malcolmson, S. J.; Li, B.; Schrock, R. R.; Hoveyda, A. H. J. Am. Chem. Soc. 2009, 131, 16407-16409 Enantioselective ring opening-cross metathesis: Ibrahem, I.; Yu, M.; Schrock, R. R.; Hoveyda, A. H. J. Am. Chem. Soc. 2009, 131, 3844-3845 Ring-opening metathesis polymerization: Flook, M. M.; Jiang, A. J.; Schrock, R. R.; Hoveyda, A. H. J. Am. Chem. Soc. 2009, 131, 7962-7963
8. Flook, M. M.; Gerber, L. C. H.; Debelouchina, G. T.; Schrock, R. R. Macromolecules 2010, 43, 7515-7522 Ethenolysis reactions: Marinescu, S. C.; Schrock, R. R.; Müller, P.; Hoveyda, A. H. J. Am. Chem. Soc. 2009, 131, 10840-10841
9. Jiang, A. J.; Zhao, Y.; Hoveyda, A. H.; Schrock, R. R. J. Am. Chem. Soc. 2009, 131, 16630-16631
10. Jiang, A. J.; Simpson, J. H.; Müller, P.; Schrock, R. R. J. Am. Chem. Soc. 2009, 131, 7770-7780
11. Schrock, R. R.; King, A. J.; Marinescu, S. C.; Simpson, J. H.; Müller, P. Organometallics 2010, 29, 5241-5251
12. Singh, R.; Schrock, R. R.; Müller, P.; Hoveyda, A. H. J. Am. Chem. Soc. 2007, 129, 12654-12655
13. Lee, Y.-J.; Schrock, R. R.; Hoveyda, A. H. J. Am. Chem. Soc. 2009, 131, 10652-10661
14. Diver, S. T.; Giessert, A. J. Chem. Rev. 2004, 104, 1317-1382
15. Schrock, R. R. In Metathesis Polymerization of Olefins and Polymerization of Alkynes; Imamoglu, Y., Ed.; Kluwer: Norwell, MA, 1998; p 357.
16. Schrock, R. R.; Luo, S.; Lee, J. C., Jr.; Zanetti, N. C.; Davis, W. M. J. Am. Chem. Soc. 1996, 118, 3883-3895
17. Fox, H. H.; Schrock, R. R. Organometallics 1992, 11, 2763-2765
18. 6 complexes.
19. Other catalysts possessing a methyl ether of the other chiral diols were also tested; metathesis reactions with such complexes proved to be less enantioselective. See the Supporting Information for more screening data.