A ruthenium-catalyzed hydrative cyclization and [4 + 2] cycloaddition of yne-enones [1]

Journal of the American Chemical Society

Volumn 122, Issue 24, 2000, Pages 5877-5878

  Trost, Barry M ^a   Brown, Rebecca E ^a   Toste, F Dean ^a  

^a STANFORD UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ALKYNE; HETEROCYCLIC COMPOUND; KETONE; RUTHENIUM;

CATALYSIS; CHEMICAL BOND; CYCLIZATION; LETTER; REACTION ANALYSIS; STRUCTURE ANALYSIS;

EID: 0034697670     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja000314m     Document Type: Letter

References (30)

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8. Doucet, H.; Martin-Vaca, B.; Bruneau, C.; Dixneuf, P. H. J. Org. Chem. 1995, 60, 7247; Trost, B. M.; Pinkerton, A. J. Am. Chem. Soc. 1999, 121, 1988; Tokumaga, M.; Wakatsuki, Y. Angew. Chem., Int. Ed. 1998, 37, 2867.
9. Trost, B. M.; Martinez, J. A.; Kulawiec, R. J.; Indolese, A. F. J. Am. Chem. Soc. 1993, 115, 10402; Trost, B. M.; Indolese, A. F.; Müller, T. J. J.; Treptow, B. J. Am. Chem. Soc. 1995, 117, 615; Trost, B. M.; Müller, T. J. J.; Martinez, J. J. Am. Chem. Soc. 1995, 117, 1888. See also: Denen, S.; Jan, D.; Dixneuf, P. H. Tetrahedron 1996, 52, 5511.
10. Trost, B. M.; Martinez, J. A.; Kulawiec, R. J.; Indolese, A. F. J. Am. Chem. Soc. 1993, 115, 10402; Trost, B. M.; Indolese, A. F.; Müller, T. J. J.; Treptow, B. J. Am. Chem. Soc. 1995, 117, 615; Trost, B. M.; Müller, T. J. J.; Martinez, J. J. Am. Chem. Soc. 1995, 117, 1888. See also: Denen, S.; Jan, D.; Dixneuf, P. H. Tetrahedron 1996, 52, 5511.
11. Trost, B. M.; Martinez, J. A.; Kulawiec, R. J.; Indolese, A. F. J. Am. Chem. Soc. 1993, 115, 10402; Trost, B. M.; Indolese, A. F.; Müller, T. J. J.; Treptow, B. J. Am. Chem. Soc. 1995, 117, 615; Trost, B. M.; Müller, T. J. J.; Martinez, J. J. Am. Chem. Soc. 1995, 117, 1888. See also: Denen, S.; Jan, D.; Dixneuf, P. H. Tetrahedron 1996, 52, 5511.
12. Trost, B. M.; Martinez, J. A.; Kulawiec, R. J.; Indolese, A. F. J. Am. Chem. Soc. 1993, 115, 10402; Trost, B. M.; Indolese, A. F.; Müller, T. J. J.; Treptow, B. J. Am. Chem. Soc. 1995, 117, 615; Trost, B. M.; Müller, T. J. J.; Martinez, J. J. Am. Chem. Soc. 1995, 117, 1888. See also: Denen, S.; Jan, D.; Dixneuf, P. H. Tetrahedron 1996, 52, 5511.
13. For an alternative cyclization of alkynyl enones catalyzed by nickel complexes, see: Jeongbeob, S.; Chui, H. M. P.; Heeg, J.; Montgomery, J. J. Am. Chem. Soc. 1999, 121, 476; Montgomery, J.; Oblinger, E.; Savchenko, A. J. Am. Chem. Soc. 1997, 119, 4911; Montgomery, J.; Chevliakev, M. V.; Brielmann, H. L. Tetrahedron 1997, 53, 16449; Montgomery, J.; Savchenko, A. J. Am. Chem. Soc. 1996, 118, 2099.
14. For an alternative cyclization of alkynyl enones catalyzed by nickel complexes, see: Jeongbeob, S.; Chui, H. M. P.; Heeg, J.; Montgomery, J. J. Am. Chem. Soc. 1999, 121, 476; Montgomery, J.; Oblinger, E.; Savchenko, A. J. Am. Chem. Soc. 1997, 119, 4911; Montgomery, J.; Chevliakev, M. V.; Brielmann, H. L. Tetrahedron 1997, 53, 16449; Montgomery, J.; Savchenko, A. J. Am. Chem. Soc. 1996, 118, 2099.
15. For an alternative cyclization of alkynyl enones catalyzed by nickel complexes, see: Jeongbeob, S.; Chui, H. M. P.; Heeg, J.; Montgomery, J. J. Am. Chem. Soc. 1999, 121, 476; Montgomery, J.; Oblinger, E.; Savchenko, A. J. Am. Chem. Soc. 1997, 119, 4911; Montgomery, J.; Chevliakev, M. V.; Brielmann, H. L. Tetrahedron 1997, 53, 16449; Montgomery, J.; Savchenko, A. J. Am. Chem. Soc. 1996, 118, 2099.
16. For an alternative cyclization of alkynyl enones catalyzed by nickel complexes, see: Jeongbeob, S.; Chui, H. M. P.; Heeg, J.; Montgomery, J. J. Am. Chem. Soc. 1999, 121, 476; Montgomery, J.; Oblinger, E.; Savchenko, A. J. Am. Chem. Soc. 1997, 119, 4911; Montgomery, J.; Chevliakev, M. V.; Brielmann, H. L. Tetrahedron 1997, 53, 16449; Montgomery, J.; Savchenko, A. J. Am. Chem. Soc. 1996, 118, 2099.
17. Trost, B. M.; Toste, F. D. Tetrahedron Lett. 1999, 40, 7739; Trost, B. M.; Toste, F. D. J. Am. Chem. Soc., 2000, 122, 714.
18. Trost, B. M.; Toste, F. D. Tetrahedron Lett. 1999, 40, 7739; Trost, B. M.; Toste, F. D. J. Am. Chem. Soc., 2000, 122, 714.
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20. All new compounds have been characterized spectroscopically, and elemental composition has been established by combustion analysis or high-resolution mass spectrometry.
21. Cf. Hartwig, J. F.; Andersen, R. A.; Bergman, R. G. J. Am. Chem. Soc. 1990, 112, 5670; Hartwig, J. F.; Bergman, R. G.; Andersen, R. A. Organometallics 1991, 10, 3326, 3344.
22. Cf. Hartwig, J. F.; Andersen, R. A.; Bergman, R. G. J. Am. Chem. Soc. 1990, 112, 5670; Hartwig, J. F.; Bergman, R. G.; Andersen, R. A. Organometallics 1991, 10, 3326, 3344.
23. For an example of O-alkylation of Ru enolates, see: Rasley, B. T.; Rapta, M.; Kulawiec, R. J. Organometallics 1996, 15, 2852.
24. For leading references of reductive elimination from Pd to form diaryl ethers and aryl alkyl ethers, see: Aranyos, A.; Old, D. W.; Kiyomori, A.; Wolfe, J. P.; Sadighi, J. P.; Buchwald, S. L. J. Am. Chem. Soc. 1999, 121, 4369; Mann, G.; Incarvito, C.; Rheingold, A. L.; Hartwig, J. F. J. Am. Chem. Soc. 1999, 121, 3224 and references therein.
25. For leading references of reductive elimination from Pd to form diaryl ethers and aryl alkyl ethers, see: Aranyos, A.; Old, D. W.; Kiyomori, A.; Wolfe, J. P.; Sadighi, J. P.; Buchwald, S. L. J. Am. Chem. Soc. 1999, 121, 4369; Mann, G.; Incarvito, C.; Rheingold, A. L.; Hartwig, J. F. J. Am. Chem. Soc. 1999, 121, 3224 and references therein.
26. For use of 1,5-diketones in synthesis, see: Heathcock, C. H.; Comprehensive Organic Synthesis; Trost, B. M.; Fleming, I.; Heathcock, C. H., Eds.; Pergamon Press: Oxford, 1991; Vol. 2, Chapter 1.5, pp 133-179; Jung, M. E. Tetrahedron 1976, 32, 3; Gawley, R. E. Synthesis 1976, 7777.
27. For use of 1,5-diketones in synthesis, see: Heathcock, C. H.; Comprehensive Organic Synthesis; Trost, B. M.; Fleming, I.; Heathcock, C. H., Eds.; Pergamon Press: Oxford, 1991; Vol. 2, Chapter 1.5, pp 133-179; Jung, M. E. Tetrahedron 1976, 32, 3; Gawley, R. E. Synthesis 1976, 7777.
28. For use of 1,5-diketones in synthesis, see: Heathcock, C. H.; Comprehensive Organic Synthesis; Trost, B. M.; Fleming, I.; Heathcock, C. H., Eds.; Pergamon Press: Oxford, 1991; Vol. 2, Chapter 1.5, pp 133-179; Jung, M. E. Tetrahedron 1976, 32, 3; Gawley, R. E. Synthesis 1976, 7777.
29. To our knowledge, this represents the first example of a heteroatom Diels-Alder reaction between an enone and an unactivated alkyne. For ruthenium catalysis of normal Diels-Alder reactions, see: Kundig, E. P.; Saudan, C. M.; Bernardinelli, G. Angew. Chem., Int. Ed. 1999, 38, 1220.
30. For a review, see: Naota, T.; Takaya, H.; Murahashi, S.-I. Chem. Rev. 1998, 98, 2599.