(Alkylthio)alkynes as addends in the Co(0) catalyzed intramolecular pauson-khand reaction. Substituent driven enhancements of annulation efficiency and stereoselectivity

Synthesis

Volumn , Issue 7, 2000, Pages 1009-1019

  Pagenkopf, Brian L ^a,b   Belanger, David B ^a,c   O'Mahony, Donogh J R ^a,d   Livinghouse, Tom ^a  

^a MONTANA STATE UNIVERSITY   (United States)

^b UNIVERSITY OF TEXAS AT AUSTIN   (United States)

^c ALCON RESEARCH LTD   (United States)

^d Systems Integrated Drug Discovery Co   (United States)

Author keywords

Annulations; Carbonylations; Catalysis; Diastereoselectivity; Sulfides

Indexed keywords

ALKYNE DERIVATIVE; COBALT;

ARTICLE; CATALYSIS; CHEMICAL REACTION; CHEMICAL STRUCTURE; MOLECULAR INTERACTION; REACTION ANALYSIS; STEREOCHEMISTRY;

EID: 0033949371     PISSN: 00397881     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2000-6301     Document Type: Article

References (23)

1. (a) Geis, O.; Schmalz, H. G. Angew. Chem., Int. Ed. 1998, 37, 911.
2. (b) Shore, N. E. In Comprehensive Organometallic Chemistry II, Vol. 12; Hegedus, L. S., Ed.; Elsevier: Oxford, 1995, p 703.
3. Pagenkopf, B. L.; Livinghouse, T. J. Am. Chem. Soc. 1996, 118, 2285.
4. (a) Belanger, D. B.; O'Mahony, D. J. R.; Livinghouse, T. Tetrahedron Lett. 1998, 39, 7636.
5. (b) Belanger, D. B.; Livinghouse, T. Tetrahedron Lett. 1998, 39, 7641.
6. Hicks, F. A.; Kablaoui, N. M.; Buchwald, S. L. J. Am. Chem. Soc. 1999, 121, 5881.
7. (a) Kondo, T.; Suzuki, N.; Okada, T.; Mitsudo, T. J. Am. Chem. Soc. 1997, 119, 6187.
8. (b) Morimoto, T.; Chatani, N.; Fukumoto, Y.; Murai, S. J. Org. Chem. 1997, 62, 3762.
9. (a) Jeong, N.; Lee, S.; Sung, B. K. Organometallics 1998, 17, 3642.
10. (b) Koga, Y.; Kobayashi, T.; Narasaka, K. Chem. Lett. 1998, 249.
11. Magnus, P; Principe, L. M.; Slater, M. J. J. Org. Chem. 1987, 52, 1483.
12. Van Wagenen, B. C.; Livinghouse, T. Tetrahedron Lett. 1989, 30, 3495.
13. For PK reactions with sulfur tethered alkynes, see: Krafft, M. E.; Scott, I. L.; Romero, R. H.; Feibelmann, S.; Vanpelt, C. E. J. Am. Chem. Soc. 1993, 114, 7199.
14. For a recent utilization of enantio-enriched vinyl sulfoxides in the stoichiometric PKR, see: Adrio, J.; Carreyero, C. J. Am. Chem. Soc. 1999, 121, 7411.
15. Krafft, M. E.; Wilson, A, M.; Dasse, O. A.; Shao, B.; Cheung, Y. Y.; Fu, Z.; Bonaga, L. V. R.; Mollman, M. K. J. Am. Chem. Soc. 1996, 118, 6080.
16. The use of trifluoroethanol (TFE) as a solvent or primary co-solvent often results in substantial improvements in the efficiency of carbonylative annulation for representative Co(0) catalyzed Pauson-Khand reactions. Details concerning the TFE solvent effect will be published separately.
17. The (t-butylthio)alkynes or (methylthio)alkynes are conveniently prepared by deprotonation with n-BuLi, or LDA [THF, -78 °C] followed by electrophilic trapping with t-butylthiocyanate, or S-(t-butyl)thiotosylate, or methylthiocyanate.
18. Bayon, J. C.; Claver, C.; Masdeu-Bulto, A. M. Coord. Chem. Rev. 1999, 195, 73.
19. (a) Ahmar, M.; Locatelli, C.; Colombier, D.; Cazes, B. Tetrahedron Lett. 1997, 38, 5281.
20. (b) Brummond, K. M.; Wan, H. H.; Kent, J. L. J. Org. Chem. 1998, 63, 6435.
21. (c) Kent, J. L.; Wan, H. H.; Brummond, K. M. Tetrahedron Lett. 1995, 36, 2407.
22. Pagenkopf, B. L.; Lund, E. C.; Livinghouse, T. Tetrahedron 1995, 51, 4421.
23. Kataoka, T.; Yoshimatsu, M.; Noda, Y.; Sato, T.; Shimizu, H.; Hori, M. J. Chem. Soc., Perkin Trans. 1 1993, 1, 121.