On the synthesis of Z-γ-amino-α,β-unsaturated esters via Ru-catalyzed coupling

Organic Letters

Volumn 1, Issue 1, 1999, Pages 67-70

  Tros, Barry M ^a   Roth, Gerald J ^a  

^a STANFORD UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ALKENE; ALKYNE; AMIDE; ESTER; RUTHENIUM; TIN;

ARTICLE; CATALYSIS; CHEMISTRY; CYCLIZATION; OXIDATION REDUCTION REACTION; SYNTHESIS;

ALKENES; ALKYNES; AMIDES; CATALYSIS; CYCLIZATION; ESTERS; OXIDATION-REDUCTION; RUTHENIUM; TIN;

EID: 0033564988     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol990547m     Document Type: Article

References (25)

1. Trost, B. M. Science 1991, 254, 1471. Trost, B. M. Angew. Chem., Int. Ed. Engl. 1995, 34, 259.
2. Trost, B. M. Science 1991, 254, 1471. Trost, B. M. Angew. Chem., Int. Ed. Engl. 1995, 34, 259.
3. For reviews, see: Hoffman, H. M. R. Angew. Chem., Int. Ed. Engl. 1969, 8, 557. Oppolzer, W.; Snieckus, V. Angew. Chem., Int. Ed. Engl. 1978, 17, 476. Snider, B. B. Acc. Chem. Res. 1980, 13, 426. Taber, D. F. Intramolecular Diels-Alder and Alder Ene Reactions; Springer-Verlag: Berlin, 1984. Snider, B. B. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Paquette, L. A., Eds.; Pergamon Press: Oxford, U.K., 1991; Vol. 5, pp 1-28. Snider, B. B. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Heathcock, C. H., Eds.; Pergamon Press: Oxford, U.K.; 1991; Vol. 2, pp 527-561.
4. For reviews, see: Hoffman, H. M. R. Angew. Chem., Int. Ed. Engl. 1969, 8, 557. Oppolzer, W.; Snieckus, V. Angew. Chem., Int. Ed. Engl. 1978, 17, 476. Snider, B. B. Acc. Chem. Res. 1980, 13, 426. Taber, D. F. Intramolecular Diels-Alder and Alder Ene Reactions; Springer-Verlag: Berlin, 1984. Snider, B. B. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Paquette, L. A., Eds.; Pergamon Press: Oxford, U.K., 1991; Vol. 5, pp 1-28. Snider, B. B. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Heathcock, C. H., Eds.; Pergamon Press: Oxford, U.K.; 1991; Vol. 2, pp 527-561.
5. For reviews, see: Hoffman, H. M. R. Angew. Chem., Int. Ed. Engl. 1969, 8, 557. Oppolzer, W.; Snieckus, V. Angew. Chem., Int. Ed. Engl. 1978, 17, 476. Snider, B. B. Acc. Chem. Res. 1980, 13, 426. Taber, D. F. Intramolecular Diels-Alder and Alder Ene Reactions; Springer-Verlag: Berlin, 1984. Snider, B. B. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Paquette, L. A., Eds.; Pergamon Press: Oxford, U.K., 1991; Vol. 5, pp 1-28. Snider, B. B. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Heathcock, C. H., Eds.; Pergamon Press: Oxford, U.K.; 1991; Vol. 2, pp 527-561.
6. For reviews, see: Hoffman, H. M. R. Angew. Chem., Int. Ed. Engl. 1969, 8, 557. Oppolzer, W.; Snieckus, V. Angew. Chem., Int. Ed. Engl. 1978, 17, 476. Snider, B. B. Acc. Chem. Res. 1980, 13, 426. Taber, D. F. Intramolecular Diels-Alder and Alder Ene Reactions; Springer-Verlag: Berlin, 1984. Snider, B. B. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Paquette, L. A., Eds.; Pergamon Press: Oxford, U.K., 1991; Vol. 5, pp 1-28. Snider, B. B. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Heathcock, C. H., Eds.; Pergamon Press: Oxford, U.K.; 1991; Vol. 2, pp 527-561.
7. For reviews, see: Hoffman, H. M. R. Angew. Chem., Int. Ed. Engl. 1969, 8, 557. Oppolzer, W.; Snieckus, V. Angew. Chem., Int. Ed. Engl. 1978, 17, 476. Snider, B. B. Acc. Chem. Res. 1980, 13, 426. Taber, D. F. Intramolecular Diels-Alder and Alder Ene Reactions; Springer-Verlag: Berlin, 1984. Snider, B. B. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Paquette, L. A., Eds.; Pergamon Press: Oxford, U.K., 1991; Vol. 5, pp 1-28. Snider, B. B. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Heathcock, C. H., Eds.; Pergamon Press: Oxford, U.K.; 1991; Vol. 2, pp 527-561.
8. For reviews, see: Hoffman, H. M. R. Angew. Chem., Int. Ed. Engl. 1969, 8, 557. Oppolzer, W.; Snieckus, V. Angew. Chem., Int. Ed. Engl. 1978, 17, 476. Snider, B. B. Acc. Chem. Res. 1980, 13, 426. Taber, D. F. Intramolecular Diels-Alder and Alder Ene Reactions; Springer-Verlag: Berlin, 1984. Snider, B. B. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Paquette, L. A., Eds.; Pergamon Press: Oxford, U.K., 1991; Vol. 5, pp 1-28. Snider, B. B. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Heathcock, C. H., Eds.; Pergamon Press: Oxford, U.K.; 1991; Vol. 2, pp 527-561.
9. Trost, B. M.; Indolese, A. F.; Müller, T. J. J.; Treptow, B. J. Am. Chem. Soc. 1995, 117, 615.
10. Trost, B. M.; Müller, T. J. J.; Martinez, J. J. Am. Chem. Soc. 1995, 117, 1888.
11. For review, see: Thomas, E. J. Acc. Chem. Res. 1991, 24, 229.
12. McNulty, J.; Still, I. W. J. Synth. Commun. 1992, 22, 979.
13. Fehrentz, J.-A.; Castro, B. Synthesis 1983, 676.
14. For a review, see: Jurczak, J.; Golebiowski, A. Chem. Rev. 1989, 89, 149.
15. Müller, S.; Liepold, B.; Roth, G. J.; Bestmann, H. J. Synlett 1996, 521. Roth, G. J.; Bestmann, H. J. Unpublished results.
16. Müller, S.; Liepold, B.; Roth, G. J.; Bestmann, H. J. Synlett 1996, 521. Roth, G. J.; Bestmann, H. J. Unpublished results.
17. For a discussion of the issue of racemization in related work, see: Ito, A.; Takahashi, R.; Baba, Y. Chem. Pharm. Bull. 1975, 23, 3081. Hanske, J. R.; Dorff, P.; Julin, S.; Martinelli, G.; Bussolari, J. Tetrahedron Lett. 1992, 33, 3715. Reginato, G.; Mordini, A.; Messina, F.; Degl'Innocenti, A.; Poli, G. Tetrahedron 1996, 52, 10985.
18. For a discussion of the issue of racemization in related work, see: Ito, A.; Takahashi, R.; Baba, Y. Chem. Pharm. Bull. 1975, 23, 3081. Hanske, J. R.; Dorff, P.; Julin, S.; Martinelli, G.; Bussolari, J. Tetrahedron Lett. 1992, 33, 3715. Reginato, G.; Mordini, A.; Messina, F.; Degl'Innocenti, A.; Poli, G. Tetrahedron 1996, 52, 10985.
19. For a discussion of the issue of racemization in related work, see: Ito, A.; Takahashi, R.; Baba, Y. Chem. Pharm. Bull. 1975, 23, 3081. Hanske, J. R.; Dorff, P.; Julin, S.; Martinelli, G.; Bussolari, J. Tetrahedron Lett. 1992, 33, 3715. Reginato, G.; Mordini, A.; Messina, F.; Degl'Innocenti, A.; Poli, G. Tetrahedron 1996, 52, 10985.
20. Reetz, M. T.; Strack, T. J.; Kanand, J.; Goddard, R. Chem. Commun. 1996, 733.
21. Cf. Trost, B. M.; Portnoy, M.; Kurihara, H. J. Am. Chem. Soc. 1997, 119, 836.
22. The triene 15 was prepared by the reaction of 10-undecenal with diethyl (E)-crotylphosphonate in the presence of KHMDS in THF.
23. Cf. Trost, B. M.; Martinez, J. A.; Kulawiec, R. J.; Indolese, A. F. J. Am. Chem. Soc. 1993, 115, 10402.
24. Otera, J.; Dan-oh, N.; Nozaki, H. J. Org. Chem. 1991, 56, 5307.
25. Earl, R. A.; Vollhardt, K. P. C. J. Am. Chem. Soc. 1983, 105, 6991.