Tandem Reactions to Construct Heterocycles via Phosphine-Catalyzed Umpolung Addition and Intramolecular Conjugate Addition

Organic Letters

Volumn 4, Issue 26, 2002, Pages 4677-4679

  Lu, Cheng ^a   Lu, Xiyan ^a  

^a SHANGHAI INSTITUTE OF ORGANIC CHEMISTRY   (China)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0013180033     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol0270733     Document Type: Article

References (26)

1. Newkome, G. R.; Paudler, W. W. Contemporary Heterocyclic Chemistry: Syntheses, Reactions and Application; Wiley: New York, 1982.
2. Ho, T.-L. Tandem Organic Reactions; Wiley: New York, 1992.
3. (a) Trost, B. M.; Li, C. J. J. Am. Chem. Soc. 1994, 116, 3167.
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9. (g) Alvarez-Ibarra, C.; Csáky, A. G.; de la Oliva, C. G. Tetrahedron Lett. 1999, 40, 8465.
10. For recent reports on phosphine-catalyzed reactions, see: (a) Wang, L.-C.; Luis, A. L.; Agapiou, K.; Jang, H.; Krische, M. J. J. Am. Chem. Soc. 2002, 124, 2402. (b) Frank, S. A.; Mergott, D. J.; Roush, W. R. J. Am. Chem. Soc. 2002, 124, 2404.
11. For recent reports on phosphine-catalyzed reactions, see: (a) Wang, L.-C.; Luis, A. L.; Agapiou, K.; Jang, H.; Krische, M. J. J. Am. Chem. Soc. 2002, 124, 2402. (b) Frank, S. A.; Mergott, D. J.; Roush, W. R. J. Am. Chem. Soc. 2002, 124, 2404.
12. (a) Trost et al. reported that the ring-opening product of the γ-adduct of Meldrum's acid and alkynone was sufficiently active to effect cyclization to afford γ-butyrolactone; see ref 3a.
13. (b) Liu et al. reported a phosphinecatalyzed annulation of thioamides and 2-alkynoates or 2,3-dienoates for constructing substituted thiazolines; see: Liu, B.; Davis, R.; Joshi, B.; Reynolds, D. W. J. Org. Chem. 2002, 67, 4595.
14. For phosphine-catalyzed conjugate addition to electron-deficient alkenes, see: (a) White, D. A.; Baizer, M. M. Tetrahedron Lett, 1973, 3597. (b) Yoshida, T.; Saito, S. Chem. Lett. 1982, 1587. (c) Gómez-Bengoa, E.; Cueva, J. M.; Mateo, C.; Echavarren, A. M. J. Am. Chem. Soc. 1996, 118, 8553. (d) Lumbierres, M.; Marchi, C.; Moreno-Mañas, M.; Sebastián, R. M.; Vallribera, A.; Lago, E.; Molins, E. Eur. J. Org. Chem. 2001, 2321.
15. For phosphine-catalyzed conjugate addition to electron-deficient alkenes, see: (a) White, D. A.; Baizer, M. M. Tetrahedron Lett, 1973, 3597. (b) Yoshida, T.; Saito, S. Chem. Lett. 1982, 1587. (c) Gómez-Bengoa, E.; Cueva, J. M.; Mateo, C.; Echavarren, A. M. J. Am. Chem. Soc. 1996, 118, 8553. (d) Lumbierres, M.; Marchi, C.; Moreno-Mañas, M.; Sebastián, R. M.; Vallribera, A.; Lago, E.; Molins, E. Eur. J. Org. Chem. 2001, 2321.
16. For phosphine-catalyzed conjugate addition to electron-deficient alkenes, see: (a) White, D. A.; Baizer, M. M. Tetrahedron Lett, 1973, 3597. (b) Yoshida, T.; Saito, S. Chem. Lett. 1982, 1587. (c) Gómez-Bengoa, E.; Cueva, J. M.; Mateo, C.; Echavarren, A. M. J. Am. Chem. Soc. 1996, 118, 8553. (d) Lumbierres, M.; Marchi, C.; Moreno-Mañas, M.; Sebastián, R. M.; Vallribera, A.; Lago, E.; Molins, E. Eur. J. Org. Chem. 2001, 2321.
17. For phosphine-catalyzed conjugate addition to electron-deficient alkenes, see: (a) White, D. A.; Baizer, M. M. Tetrahedron Lett, 1973, 3597. (b) Yoshida, T.; Saito, S. Chem. Lett. 1982, 1587. (c) Gómez-Bengoa, E.; Cueva, J. M.; Mateo, C.; Echavarren, A. M. J. Am. Chem. Soc. 1996, 118, 8553. (d) Lumbierres, M.; Marchi, C.; Moreno-Mañas, M.; Sebastián, R. M.; Vallribera, A.; Lago, E.; Molins, E. Eur. J. Org. Chem. 2001, 2321.
18. For stoichiometric multistep additions on vinyl-triphenylphosphonium salt to afford heterocycles, see: Cristau, H. J.; Fonte, M.; Torreiles, E. Synthesis 1989, 301 and references therein.
19. Typical reaction conditions: to a solution of a bifunctional nucleophile (0.5 mmol) and triphenylphosphine (0.1 mol) in toluene (1.5 mL) at the indicated temperature under nitrogen was added a solution of an electron-deficient allene or alkyne (0.5 mmol) in toluene (1 mL).
20. Structure of compound 51 was confirmed by X-ray crystallography, indicating that the tandem nucleophilic addition reactions of oxygen-nitrogen bifunctional nucleophile with electron-deficient alkyne started from the nitrogen nucleophilic center.
21. For synthesis of piperazine-2-carboxylic acid, see: (a) Mérour, J. Y.; Coadou, J. Y. Tetrahedron Lett. 1991, 32, 2469. (b) Bigge, C. F.; Hays, S. J.; Novak, P. M.; Drummond, J. T.; Johnson, G.; Bobovski, T. P. Tetrahedron Lett. 1989, 30, 5193.
22. For synthesis of piperazine-2-carboxylic acid, see: (a) Mérour, J. Y.; Coadou, J. Y. Tetrahedron Lett. 1991, 32, 2469. (b) Bigge, C. F.; Hays, S. J.; Novak, P. M.; Drummond, J. T.; Johnson, G.; Bobovski, T. P. Tetrahedron Lett. 1989, 30, 5193.
23. CPP is a high-affinity competitive antagonist of the NMDA subtype of the glutamate receptor. For references, see: (a) Davis, J.; Evans, R.; Herrling, P. L.; Jones, A. W.; Olverman, H. J.; Pook, P.; Watkins, J. C. Brain Res. 1986, 382, 169. (b) Hays, S. J.; Bigge, C. F.; Novak, P. M.; Drummond, J. T.; Bobovski, T. P.; Rice, M. J.; Johnson, G.; Brachce, L. J.; Coughenour, L. L. J. Med. Chem. 1990, 10, 2916.
24. CPP is a high-affinity competitive antagonist of the NMDA subtype of the glutamate receptor. For references, see: (a) Davis, J.; Evans, R.; Herrling, P. L.; Jones, A. W.; Olverman, H. J.; Pook, P.; Watkins, J. C. Brain Res. 1986, 382, 169. (b) Hays, S. J.; Bigge, C. F.; Novak, P. M.; Drummond, J. T.; Bobovski, T. P.; Rice, M. J.; Johnson, G.; Brachce, L. J.; Coughenour, L. L. J. Med. Chem. 1990, 10, 2916.
25. An HIV protease inhibitor indinavir; for references, see: (a) Dorsey, B. D.; Levin, R. B.; McDaniel, S. L.; Vacca, J. P.; Guare, J. P.; Darke, P. L.; Zugay, J. A.; Emini, E. A.; Schleif, W. A.; Quintero, J. C.; Lin, J. H.; Chen, I. W.; Holloway, M. K.; Fizgerald, P. M. D.; Axel, M. G.; Ostovic, D.; Anderson, P. S.; Huff, J. R. J. Med. Chem. 1994, 37, 3443. (b) Hamner, S. M.; Squires, K. E.; Huges, M. D.; Grimes, J. M.; Demeter, L. M.; Currier, J. S.; Eron, J. J.; Fienbera, J. E.; Balfour, H. H.; Deyton, L. R.; Chodakewitz, J. A.; Fischl, M. A. N. Engl. J. Med. 1997, 337, 725.
26. An HIV protease inhibitor indinavir; for references, see: (a) Dorsey, B. D.; Levin, R. B.; McDaniel, S. L.; Vacca, J. P.; Guare, J. P.; Darke, P. L.; Zugay, J. A.; Emini, E. A.; Schleif, W. A.; Quintero, J. C.; Lin, J. H.; Chen, I. W.; Holloway, M. K.; Fizgerald, P. M. D.; Axel, M. G.; Ostovic, D.; Anderson, P. S.; Huff, J. R. J. Med. Chem. 1994, 37, 3443. (b) Hamner, S. M.; Squires, K. E.; Huges, M. D.; Grimes, J. M.; Demeter, L. M.; Currier, J. S.; Eron, J. J.; Fienbera, J. E.; Balfour, H. H.; Deyton, L. R.; Chodakewitz, J. A.; Fischl, M. A. N. Engl. J. Med. 1997, 337, 725.