The MARDi Cascade: A New Base-Induced Five-Step Anionic Domino Reaction for the Stereoselective Preparation of Functionalized Cycloheptenes

Journal of Organic Chemistry

Volumn 62, Issue 10, 1997, Pages 3034-3035

  Filippini, Marie Hélène ^a   Rodriguez, Jean ^a  

^a UMR au CNRS 6516   (France)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0000798527     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo970196u     Document Type: Article

References (30)

1. Tietze, L. F. Chem. Rev. 1996, 96, 115-136 and references cited therein.
2. Ho, T.-L. Tandem Organic Reactions; Wiley: New York, 1992. Tietze, L. F.; Beifuss, U. Angew. Chem. 1993, 105, 137-169; Angew. Chem., Int. Ed. Engl. 1993, 32, 131-163. Trost, B. M. Angew. Chem. 1995, 107, 285-307; Angew. Chem., Int. Ed. Engl. 1995, 34, 259-281. Bunce, R. A. Tetrahedron 1995, 51, 13103-13160. See also a special issue: Chem. Rev. 1996, 96, 1.
3. Ho, T.-L. Tandem Organic Reactions; Wiley: New York, 1992. Tietze, L. F.; Beifuss, U. Angew. Chem. 1993, 105, 137-169; Angew. Chem., Int. Ed. Engl. 1993, 32, 131-163. Trost, B. M. Angew. Chem. 1995, 107, 285-307; Angew. Chem., Int. Ed. Engl. 1995, 34, 259-281. Bunce, R. A. Tetrahedron 1995, 51, 13103-13160. See also a special issue: Chem. Rev. 1996, 96, 1.
4. Ho, T.-L. Tandem Organic Reactions; Wiley: New York, 1992. Tietze, L. F.; Beifuss, U. Angew. Chem. 1993, 105, 137-169; Angew. Chem., Int. Ed. Engl. 1993, 32, 131-163. Trost, B. M. Angew. Chem. 1995, 107, 285-307; Angew. Chem., Int. Ed. Engl. 1995, 34, 259-281. Bunce, R. A. Tetrahedron 1995, 51, 13103-13160. See also a special issue: Chem. Rev. 1996, 96, 1.
5. Ho, T.-L. Tandem Organic Reactions; Wiley: New York, 1992. Tietze, L. F.; Beifuss, U. Angew. Chem. 1993, 105, 137-169; Angew. Chem., Int. Ed. Engl. 1993, 32, 131-163. Trost, B. M. Angew. Chem. 1995, 107, 285-307; Angew. Chem., Int. Ed. Engl. 1995, 34, 259-281. Bunce, R. A. Tetrahedron 1995, 51, 13103-13160. See also a special issue: Chem. Rev. 1996, 96, 1.
6. Ho, T.-L. Tandem Organic Reactions; Wiley: New York, 1992. Tietze, L. F.; Beifuss, U. Angew. Chem. 1993, 105, 137-169; Angew. Chem., Int. Ed. Engl. 1993, 32, 131-163. Trost, B. M. Angew. Chem. 1995, 107, 285-307; Angew. Chem., Int. Ed. Engl. 1995, 34, 259-281. Bunce, R. A. Tetrahedron 1995, 51, 13103-13160. See also a special issue: Chem. Rev. 1996, 96, 1.
7. Ho, T.-L. Tandem Organic Reactions; Wiley: New York, 1992. Tietze, L. F.; Beifuss, U. Angew. Chem. 1993, 105, 137-169; Angew. Chem., Int. Ed. Engl. 1993, 32, 131-163. Trost, B. M. Angew. Chem. 1995, 107, 285-307; Angew. Chem., Int. Ed. Engl. 1995, 34, 259-281. Bunce, R. A. Tetrahedron 1995, 51, 13103-13160. See also a special issue: Chem. Rev. 1996, 96, 1.
8. Ho, T.-L. Tandem Organic Reactions; Wiley: New York, 1992. Tietze, L. F.; Beifuss, U. Angew. Chem. 1993, 105, 137-169; Angew. Chem., Int. Ed. Engl. 1993, 32, 131-163. Trost, B. M. Angew. Chem. 1995, 107, 285-307; Angew. Chem., Int. Ed. Engl. 1995, 34, 259-281. Bunce, R. A. Tetrahedron 1995, 51, 13103-13160. See also a special issue: Chem. Rev. 1996, 96, 1.
9. Filippini, M.-H.; Faure, R.; Rodriguez, J. J. Org. Chem. 1995, 60, 6872-6882.
10. Filippini, M.-H.; Rodriguez, J. J. Chem. Soc., Chem. Commun. 1995, 33-34.
11. Filippini, M.-H.; Rodriguez, J.; Santelli, M. J. Chem. Soc., Chem. Commun. 1993, 1647-1648.
12. Lavoisier, T.; Rodriguez, J. Synlett 1995, 1241-1242.
13. Lavoisier, T.; Rodriguez, J. Synlett 1996, 339-340.
14. For selected recent approaches to cycloheptenes from cyclopentanones derivatives see, inter alia: Dow, P.; Zhang, W. Chem. Rev. 1993, 93, 2091-2115. Suginome, H.; Nakayama, Y.; Harada, H.; Hachiro, H.; Orito, K. J. Chem. Soc., Chem. Commun. 1994, 451-452. Ranu, B. C.; Das, A. R. J. Chem. Soc., Perkin Trans. 1 1994, 921-922. Ruder S. M.; Norwood, B. K. Tetrahedron Lett. 1994, 35, 3473-3476. Lange G. L.; Gottardo, C. Tetrahedron Lett. 1994, 35, 8513-8516. Ruder, S. M.; Kulkarni, V. R. J. Org. Chem. 1995, 60, 3084-3091. Li, C.-J.; Chen, D.-L.; Lu, Y.-Q.; Haberman, J. X.; Mague, J. T. J. Am. Chem. Soc. 1996, 118, 4216-4217. Crimmins, M. T.; Huang, S.; Guise-Zawacki, L. E. Tetrahedron Lett. 1996, 37, 6519-6522.
15. For selected recent approaches to cycloheptenes from cyclopentanones derivatives see, inter alia: Dow, P.; Zhang, W. Chem. Rev. 1993, 93, 2091-2115. Suginome, H.; Nakayama, Y.; Harada, H.; Hachiro, H.; Orito, K. J. Chem. Soc., Chem. Commun. 1994, 451-452. Ranu, B. C.; Das, A. R. J. Chem. Soc., Perkin Trans. 1 1994, 921-922. Ruder S. M.; Norwood, B. K. Tetrahedron Lett. 1994, 35, 3473-3476. Lange G. L.; Gottardo, C. Tetrahedron Lett. 1994, 35, 8513-8516. Ruder, S. M.; Kulkarni, V. R. J. Org. Chem. 1995, 60, 3084-3091. Li, C.-J.; Chen, D.-L.; Lu, Y.-Q.; Haberman, J. X.; Mague, J. T. J. Am. Chem. Soc. 1996, 118, 4216-4217. Crimmins, M. T.; Huang, S.; Guise-Zawacki, L. E. Tetrahedron Lett. 1996, 37, 6519-6522.
16. For selected recent approaches to cycloheptenes from cyclopentanones derivatives see, inter alia: Dow, P.; Zhang, W. Chem. Rev. 1993, 93, 2091-2115. Suginome, H.; Nakayama, Y.; Harada, H.; Hachiro, H.; Orito, K. J. Chem. Soc., Chem. Commun. 1994, 451-452. Ranu, B. C.; Das, A. R. J. Chem. Soc., Perkin Trans. 1 1994, 921-922. Ruder S. M.; Norwood, B. K. Tetrahedron Lett. 1994, 35, 3473-3476. Lange G. L.; Gottardo, C. Tetrahedron Lett. 1994, 35, 8513-8516. Ruder, S. M.; Kulkarni, V. R. J. Org. Chem. 1995, 60, 3084-3091. Li, C.-J.; Chen, D.-L.; Lu, Y.-Q.; Haberman, J. X.; Mague, J. T. J. Am. Chem. Soc. 1996, 118, 4216-4217. Crimmins, M. T.; Huang, S.; Guise-Zawacki, L. E. Tetrahedron Lett. 1996, 37, 6519-6522.
17. For selected recent approaches to cycloheptenes from cyclopentanones derivatives see, inter alia: Dow, P.; Zhang, W. Chem. Rev. 1993, 93, 2091-2115. Suginome, H.; Nakayama, Y.; Harada, H.; Hachiro, H.; Orito, K. J. Chem. Soc., Chem. Commun. 1994, 451-452. Ranu, B. C.; Das, A. R. J. Chem. Soc., Perkin Trans. 1 1994, 921-922. Ruder S. M.; Norwood, B. K. Tetrahedron Lett. 1994, 35, 3473-3476. Lange G. L.; Gottardo, C. Tetrahedron Lett. 1994, 35, 8513-8516. Ruder, S. M.; Kulkarni, V. R. J. Org. Chem. 1995, 60, 3084-3091. Li, C.-J.; Chen, D.-L.; Lu, Y.-Q.; Haberman, J. X.; Mague, J. T. J. Am. Chem. Soc. 1996, 118, 4216-4217. Crimmins, M. T.; Huang, S.; Guise-Zawacki, L. E. Tetrahedron Lett. 1996, 37, 6519-6522.
18. For selected recent approaches to cycloheptenes from cyclopentanones derivatives see, inter alia: Dow, P.; Zhang, W. Chem. Rev. 1993, 93, 2091-2115. Suginome, H.; Nakayama, Y.; Harada, H.; Hachiro, H.; Orito, K. J. Chem. Soc., Chem. Commun. 1994, 451-452. Ranu, B. C.; Das, A. R. J. Chem. Soc., Perkin Trans. 1 1994, 921-922. Ruder S. M.; Norwood, B. K. Tetrahedron Lett. 1994, 35, 3473-3476. Lange G. L.; Gottardo, C. Tetrahedron Lett. 1994, 35, 8513-8516. Ruder, S. M.; Kulkarni, V. R. J. Org. Chem. 1995, 60, 3084-3091. Li, C.-J.; Chen, D.-L.; Lu, Y.-Q.; Haberman, J. X.; Mague, J. T. J. Am. Chem. Soc. 1996, 118, 4216-4217. Crimmins, M. T.; Huang, S.; Guise-Zawacki, L. E. Tetrahedron Lett. 1996, 37, 6519-6522.
19. For selected recent approaches to cycloheptenes from cyclopentanones derivatives see, inter alia: Dow, P.; Zhang, W. Chem. Rev. 1993, 93, 2091-2115. Suginome, H.; Nakayama, Y.; Harada, H.; Hachiro, H.; Orito, K. J. Chem. Soc., Chem. Commun. 1994, 451-452. Ranu, B. C.; Das, A. R. J. Chem. Soc., Perkin Trans. 1 1994, 921-922. Ruder S. M.; Norwood, B. K. Tetrahedron Lett. 1994, 35, 3473-3476. Lange G. L.; Gottardo, C. Tetrahedron Lett. 1994, 35, 8513-8516. Ruder, S. M.; Kulkarni, V. R. J. Org. Chem. 1995, 60, 3084-3091. Li, C.-J.; Chen, D.-L.; Lu, Y.-Q.; Haberman, J. X.; Mague, J. T. J. Am. Chem. Soc. 1996, 118, 4216-4217. Crimmins, M. T.; Huang, S.; Guise-Zawacki, L. E. Tetrahedron Lett. 1996, 37, 6519-6522.
20. For selected recent approaches to cycloheptenes from cyclopentanones derivatives see, inter alia: Dow, P.; Zhang, W. Chem. Rev. 1993, 93, 2091-2115. Suginome, H.; Nakayama, Y.; Harada, H.; Hachiro, H.; Orito, K. J. Chem. Soc., Chem. Commun. 1994, 451-452. Ranu, B. C.; Das, A. R. J. Chem. Soc., Perkin Trans. 1 1994, 921-922. Ruder S. M.; Norwood, B. K. Tetrahedron Lett. 1994, 35, 3473-3476. Lange G. L.; Gottardo, C. Tetrahedron Lett. 1994, 35, 8513-8516. Ruder, S. M.; Kulkarni, V. R. J. Org. Chem. 1995, 60, 3084-3091. Li, C.-J.; Chen, D.-L.; Lu, Y.-Q.; Haberman, J. X.; Mague, J. T. J. Am. Chem. Soc. 1996, 118, 4216-4217. Crimmins, M. T.; Huang, S.; Guise-Zawacki, L. E. Tetrahedron Lett. 1996, 37, 6519-6522.
21. For selected recent approaches to cycloheptenes from cyclopentanones derivatives see, inter alia: Dow, P.; Zhang, W. Chem. Rev. 1993, 93, 2091-2115. Suginome, H.; Nakayama, Y.; Harada, H.; Hachiro, H.; Orito, K. J. Chem. Soc., Chem. Commun. 1994, 451-452. Ranu, B. C.; Das, A. R. J. Chem. Soc., Perkin Trans. 1 1994, 921-922. Ruder S. M.; Norwood, B. K. Tetrahedron Lett. 1994, 35, 3473-3476. Lange G. L.; Gottardo, C. Tetrahedron Lett. 1994, 35, 8513-8516. Ruder, S. M.; Kulkarni, V. R. J. Org. Chem. 1995, 60, 3084-3091. Li, C.-J.; Chen, D.-L.; Lu, Y.-Q.; Haberman, J. X.; Mague, J. T. J. Am. Chem. Soc. 1996, 118, 4216-4217. Crimmins, M. T.; Huang, S.; Guise-Zawacki, L. E. Tetrahedron Lett. 1996, 37, 6519-6522.
22. Carrick, W.; Fry, A. J. Am. Chem. Soc. 1955, 77, 4381-4387.
23. For the first reported synthetic application of the fragmentation of related 2-aminobicyclo[3.2.1]octanones, see: Stork, G.; Landesman, H. K. J. Am. Chem. Soc. 1956, 78, 5129-5130. For a recent review, see: Filippini, M.-H.; Rodriguez, J. Synthesis, in press.
24. For the first reported synthetic application of the fragmentation of related 2-aminobicyclo[3.2.1]octanones, see: Stork, G.; Landesman, H. K. J. Am. Chem. Soc. 1956, 78, 5129-5130. For a recent review, see: Filippini, M.-H.; Rodriguez, J. Synthesis, in press.
25. 2. This purification process usually suffers from partial or extensive lost of material by some undetermined degradation process.
26. Dickson, R. S.; Kirch, H. P. Aust. J. Chem. 1972, 25, 1815-1818.
27. The study of the synthetic utility of these derivatives as potential dienophiles, Michael acceptors, and [3 + 2] cyclopentannulation partners is underway.
28. 2O has been found to be quite efficient for selective ester saponifications at room temperature, and these results will be disclosed in due course: Filippini, M.-H. Ph.D. Thesis, Marseille, September 1996.
29. Another mechanism suggested by one of the reviewers involving an intramolecular lactonization/elimination sequence from β-hydroxy cycloheptane isomers cannot be ruled out although it could not be effective with α-epimers. Chemical equations presented
30. Heats of formation, nicely provided by one of the reviewers and calculated with PCMODEL for both 1,3-cis and 1,3-trans isomers of 4a, corroborate our own results obtained from AM1/RHF (AMPAC) semiempirical calculations and showed a preference of only 1-2.2 kcal in favor of the 1,3-cis-diequatorial isomer, which corresponds to an approximate 80:20 to 95:5 mixture if thermodynamic equilibrium is achived and cannot argue alone for the complete diastereoselectivity observed.