The reaction of propiolate acetylides with nitrones. Synthesis of γ-amino-α,β-ethylenic acid derivatives

Tetrahedron Letters

Volumn 38, Issue 31, 1997, Pages 5503-5506

  Denis, Jean Noël ^a   Tchertchian, Sylvie ^a   Tomassini, Axel ^a   Vallée, Yannick ^a  

^a UNIVERSITÉ JOSEPH FOURIER   (France)

Author keywords

[No Author keywords available]

Indexed keywords

AMINO ACID DERIVATIVE; GAMMA AMINO ALPHA,BETA ETHYLENIC ACID DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; DRUG SYNTHESIS; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; REACTION ANALYSIS; STEREOCHEMISTRY;

EID: 0030792964     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(97)01210-0     Document Type: Article

References (18)

1. Confalone, P. N.; Huie, E. M. Org. React., 1988, 36, 1-173. Dondoni, A.; Franco, S.; Junquera, F.; Merchàn, F. L.; Merino, P.; Tejero, T.; Bertolasi, V. Chem. Eur. J., 1995, 1, 505-520.
2. Confalone, P. N.; Huie, E. M. Org. React., 1988, 36, 1-173. Dondoni, A.; Franco, S.; Junquera, F.; Merchàn, F. L.; Merino, P.; Tejero, T.; Bertolasi, V. Chem. Eur. J., 1995, 1, 505-520.
3. Delgado-Escueta, A. V.; Ward, A. A., Jr.; Woodbury, D. M.; Porter, R. J. Basic Mechanisms of the Epilepsies, Raven Press, New York, 1986, pp. 365-378.
4. Wei, Z.-Y.; Knaus, E. E. Tetrahedron, 1994, 50, 5569-5578. Margolin, A. L. Tetrahedron Lett., 1993, 34, 1239-1242.
5. Wei, Z.-Y.; Knaus, E. E. Tetrahedron, 1994, 50, 5569-5578. Margolin, A. L. Tetrahedron Lett., 1993, 34, 1239-1242.
6. Burke, J. R.; Silverman, R. B. J. Am. Chem. Soc., 1991, 113, 9329-9340.
7. The thrombin inhibitor cyclotheonamide B contains a γ-amino-α,β-ethylenic acid fragment: Hagihara, M.; Schreiber, S. L. J. Am. Chem. Soc., 1992, 114, 6570-6571.
8. Simonyi, M. Enantiomer, 1996, 1, 403-414.
9. The cytotoxic calyculins, isolated from Discodermia calyx, contain a γ-amino-α,β-dihydroxyacid fragment: Hamada, Y.; Tanada, Y.; Yokokawa, F.; Shiori, T. Tetrahedron Lett., 1991, 32, 5983-5986.
10. Experimental procedure: To a solution of tert-butyl propiolate (1.45 mmol) in dry THF stirred under a nitrogen atmosphere was added slowly at -78°C a solution of n-BuLi in hexane (1.6 M, 1.42 mmol). After 1h, a solution of the nitrone (1 mmol) in THF was added. The resulting solution was stirred at -78°C for a period determined by TLC (see table). Then the reaction mixture was quenched with water and extracted with EtOAc. After a conventional work-up, the hydroxylamine was purified by chromatography on silica gel (eluent: pentane/ethyl acetate mixtures).
11. Wuts, P. G. M.; Jung, Y.-W. J. Org. Chem., 1988, 53, 1957-1965.
12. 2 = t-Bu), we were able to isolate the non-cyclized Z-amino ethylenic ester in 60% yield (conditions: 20 eq. Zn, AcOH/MeOH: 1/9, 100mn, 60°C)
13. Merino, P.; Anoro, S.; Castillo, E.; Merchan, F.; Tejero, T. Tetrahedron: Asym., 1996, 7, 1887-1890.
14. Dondoni, A.; Franco, S., Junquera, F. L.; Merchàn, F., Merino, P.; Tejero, T. Synth. Commun., 1994, 24, 2537-2550.
15. 3C).
16. 2 = t-Bu) was determined by X-ray analysis of a single crystal. This structure will be published soon.
17. 3JCHOH,CHN ≈ 0 Hz): Gaudemer, A. in Stereochemistry, Fundamentals and Methods, Kagan, H, Ed., Georg Thieme Publishers: Stuttgart, 1977, vol. 1, pp. 44-136. See also: Rassu, G.; Casiraghi, G.; Spanu, P.; Pinna, L.; Fava, G. G.; Ferrari, M. B.; Pelosi, G. Tetrahedron: Asym., 1992, 3, 1035-1048.
18. 3JCHOH,CHN ≈ 0 Hz): Gaudemer, A. in Stereochemistry, Fundamentals and Methods, Kagan, H, Ed., Georg Thieme Publishers: Stuttgart, 1977, vol. 1, pp. 44-136. See also: Rassu, G.; Casiraghi, G.; Spanu, P.; Pinna, L.; Fava, G. G.; Ferrari, M. B.; Pelosi, G. Tetrahedron: Asym., 1992, 3, 1035-1048.