Comparison of Ru- and Mo-based chiral olefin metathesis catalysts. Complementarity in asymmetric ring-opening/cross-metathesis reactions of oxa- and azabicycles

Organic Letters

Volumn 9, Issue 15, 2007, Pages 2871-2874

  Cotez, G Alex ^a   Baxter, Carl A ^a   Schrock, Richard R ^b   Hoveyda, Amir H ^a  

^a BOSTON COLLEGE   (United States)

^b MASSACHUSETTS INSTITUTE OF TECHNOLOGY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ALKENE; BICYCLO COMPOUND; MOLYBDENUM; RUTHENIUM;

ARTICLE; CATALYSIS; CHEMISTRY; COMPARATIVE STUDY; STEREOISOMERISM;

ALKENES; BICYCLO COMPOUNDS; CATALYSIS; MOLYBDENUM; RUTHENIUM; STEREOISOMERISM;

EID: 34547174193     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol071008h     Document Type: Article

References (28)

1. For reviews on catalytic olefin metathesis, see: Handbook of Metathesis; Grubbs, R. H., Ed.; Wiley-VCH: Weinheim, Germany, 2003.
2. For example, see: (a) Schneider, M. F.; Lucas, N.; Velder, J.; Blechert, S. Angew. Chem., Int. Ed. 1997, 36, 257-259.
3. (b) Chatterjee, A. K.; Choi, T.-L.; Sanders, D. P.; Grubbs, R. H. J. Am. Chem. Soc. 2003, 125, 11360-11370.
4. (c) Michrowska, A.; Bieniek, M.; Kim, M.; Klajn, R.; Grela, K. Tetrahedron 2003, 59, 4525-4531.
5. (d) Schrock, R. R.; Hoveyda, A. H. Angew. Chem., Int. Ed. 2003, 42, 4592-4633.
6. For a review on catalytic olefin metathesis methods used in the synthesis of heterocycles, see: Deiters, A.; Martin, S. F. Chem. Rev. 2004, 104, 2199-2238.
7. (a) Van Veldhuizen, J. J.; Garber, S. B.; Kingsbury, J. S.; Hoveyda, A. H. J. Am. Chem. Soc. 2002, 124, 4954-4955.
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9. For a brief overview, see: Hoveyda, A. H.; Gillingham, D. G.; Van Veldhuizen, J. J.; Kataoka, O.; Garber, S. B.; Kingsbury, J. S.; Harrity, J. P. A. Org. Biomol. Chem. 2004, 2, 8-23.
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15. (a) Zhu, S. S.; Cefalo, D. R.; La, D. S.; Jamieson, J. Y.; Davis, W. M.; Hoveyda, A. H.; Schrock, R. R. J. Am. Chem. Soc. 1999, 121, 8251-8259.
16. (b) Alexander, J. B.; Schrock, R. R.; Davis, W. M.; Hultzsch, K. C.; Hoveyda, A. H.; Houser, J. H. Organometallics 2000, 19, 3700-3715.
17. (c) Schrock, R. R.; Jamieson, J. Y.; Dolman, S. J.; Miller, S. A.; Bonitatebus, P. J., Jr.; Hoveyda, A. H. Organometallics 2002, 21, 409-417.
18. Pilyugina, T. S.; Schrock, R. R.; Müller, P.; Hoveyda, A. H. Organometallics 2007, 26, 831-837.
19. Aeilts, S. L.; Cefalo, D. R.; Bonitatebus, P. J., Jr.; Houser, J. H.; Hoveyda, A. H.; Schrock, R. R. Angew. Chem., Int. Ed. 2001, 40, 1452-1456.
20. Varying values for isolated yield is due to the volatility of pyran 9.
21. Enantioselectivity does not improve when this reaction is carried out at -15°C
22. Gillingham, D. G.; Hoveyda, A. H. Angew. Chem., Int. Ed. 2007, 46, 3860-3864.
23. Cortez, G. A.; Schrock, R. R.; Hoveyda, A. H. Angew. Chem., Int. Ed. 2007, 46, 4534-4538.
24. For another class of class Ru catalysts (monodentate NHC), see: (a) Seiders, T. J.; Ward, D. W.; Grubbs, R. H. Org. Lett. 2001, 3, 3225-3228.
25. (b) Funk, T. W.; Berlin, J. M.; Grubbs, R. H. J. Am. Chem. Soc. 2006, 128, 1840-1846.
26. These catalysts have thus far proven to be less effective in promoting AROM/CM (1.4-1:1 E:Z, 33-80% ee); see: (c) Berlin, J. M.; Goldberg, S. D.; Grubbs, R. H. Angew. Chem., Int. Ed. 2006, 45, 7591-7595.
27. For a discussion regarding the effect of competing methylidene complexes on catalytic AROM/CM reactions, see: La, D. S.; Sattely, E. S.; Ford, J. G.; Schrock, R. R.; Hoveyda, A. H. J. Am. Chem. Soc. 2001, 123, 7767-7778.
28. Giudici, R. E.; Hoveyda, A. H. J. Am. Chem. Soc. 2007, 129, 3824-3825.