Tandem catalytic asymmetric ring-opening metathesis/cross metathesis [19]

Journal of the American Chemical Society

Volumn 121, Issue 49, 1999, Pages 11603-11604

  La, Daniel S ^a   Gair Ford, J ^a   Sattely, Elizabeth S ^a   Bonitatebus, Peter J ^b   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

STYRENE;

CATALYSIS; CHEMICAL REACTION; CHEMICAL STRUCTURE; ENANTIOMER; LETTER; POLYMERIZATION; REACTION ANALYSIS; STEREOCHEMISTRY;

EID: 0342614211     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja9931832     Document Type: Letter

References (20)

1. Armstrong, S. K. J. Chem. Soc., Perkin Trans. 1 1998, 371-388.
2. For representative recent reports on Ru-catalyzed ROM, see: (a) Snapper, M. L.; Tallarico, J. A.; Randall, M. L. J. Am. Chem. Soc. 1997, 119, 9, 1478-1479. (b) Schneider, M. F.; Lucas, N.; Velder, J.; Blechert, S. Angew. Chem., Int. Ed. Engl. 1997, 36, 257-259.
3. For representative recent reports on Ru-catalyzed ROM, see: (a) Snapper, M. L.; Tallarico, J. A.; Randall, M. L. J. Am. Chem. Soc. 1997, 119, 9, 1478-1479. (b) Schneider, M. F.; Lucas, N.; Velder, J.; Blechert, S. Angew. Chem., Int. Ed. Engl. 1997, 36, 257-259.
4. (a) Crowe, W. E.; Goldberg, D. R. J. Am. Chem. Soc. 1995, 117, 5162-5163.
5. (b) For a recent review of catalytic CM, see: (b) Gibson, S. E. In Alkene Metathesis in Organic Synthesis; Furstner, A., Ed.; Springer, Berlin 1998; pp 155-180.
6. For examples of non-asymmetric tandem catalytic ROM/RCM, see: (a) Harrity, J. P. A.; La, D. S.; Cefalo, D. R.; Visser, M. S.; Hoveyda, A. H. J. Am. Chem. Soc. 1998, 120, 2343-2351. (b) Johannes, C. W.; Visser, M. S.; Weatherhead G. S.; Hoveyda, A. H. J. Am. Chem. Soc. 1998, 120, 8340- 8347. For examples of nonasymmetric tandem catalytic ROM/CM, see: (c) Randall, M. L.; Tallarico, J. A.; Snapper, M. L. J. Am. Chem. Soc. 1995, 117, 9610-9611. (d) Reference 2b.
7. For examples of non-asymmetric tandem catalytic ROM/RCM, see: (a) Harrity, J. P. A.; La, D. S.; Cefalo, D. R.; Visser, M. S.; Hoveyda, A. H. J. Am. Chem. Soc. 1998, 120, 2343-2351. (b) Johannes, C. W.; Visser, M. S.; Weatherhead G. S.; Hoveyda, A. H. J. Am. Chem. Soc. 1998, 120, 8340-8347. For examples of nonasymmetric tandem catalytic ROM/CM, see: (c) Randall, M. L.; Tallarico, J. A.; Snapper, M. L. J. Am. Chem. Soc. 1995, 117, 9610-9611. (d) Reference 2b.
8. For examples of non-asymmetric tandem catalytic ROM/RCM, see: (a) Harrity, J. P. A.; La, D. S.; Cefalo, D. R.; Visser, M. S.; Hoveyda, A. H. J. Am. Chem. Soc. 1998, 120, 2343-2351. (b) Johannes, C. W.; Visser, M. S.; Weatherhead G. S.; Hoveyda, A. H. J. Am. Chem. Soc. 1998, 120, 8340- 8347. For examples of nonasymmetric tandem catalytic ROM/CM, see: (c) Randall, M. L.; Tallarico, J. A.; Snapper, M. L. J. Am. Chem. Soc. 1995, 117, 9610-9611. (d) Reference 2b.
9. For examples of non-asymmetric tandem catalytic ROM/RCM, see: (a) Harrity, J. P. A.; La, D. S.; Cefalo, D. R.; Visser, M. S.; Hoveyda, A. H. J. Am. Chem. Soc. 1998, 120, 2343-2351. (b) Johannes, C. W.; Visser, M. S.; Weatherhead G. S.; Hoveyda, A. H. J. Am. Chem. Soc. 1998, 120, 8340- 8347. For examples of nonasymmetric tandem catalytic ROM/CM, see: (c) Randall, M. L.; Tallarico, J. A.; Snapper, M. L. J. Am. Chem. Soc. 1995, 117, 9610-9611. (d) Reference 2b.
10. (a) Alexander, J. B.; La, D. S.; Cefalo, D. R.; Hoveyda, A. H.; Schrock, R. R. J. Am. Chem. Soc. 1998, 120, 4041-4042.
11. (b) La, D. S.; Alexander, J. B.; Cefalo, D. R.; Graf, D. D.; Hoveyda, A. H.; Schrock, R. R. J. Am. Chem. Soc. 1998, 120, 9720-9721.
12. Zhu, 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.
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14. The reason for this observation is unclear at the present time.
15. The stereochemical identity of all products in Table 1 and Scheme 2 is consistent with the assignment made based on the X-ray structure (cf. Figure 1). Selected products from all substrates were converted to common intermediates (derived acetates in place of silyl or MOM ethers) and compared by chiral HPLC.
16. The difference between total conversion and conversion to product constitutes the percent byproduct formation.
17. Tamao, K.; Kobayashi, K.; Ito, Y. Tetrahedron Lett. 1989, 30, 6051-6054.
18. Crowe, W. E.; Zhang, Z. J. J. Am. Chem. Soc. 1993, 115, 10998-10999.
19. The ratio of 1a: styrene (4a) was selected so as to mimic the conditions in Table 1.
20. This research was generously supported by the NSF (CHE-9905806 to A. H. H.; CHE-9700736 to R. R. S.) and the NIH (GM-47480 to A.H.H.). D. S. L. is grateful for a graduate fellowship by the American Chemical Society (sponsored by Boehringer-Ingelheim).