Tert-butyldiphenylsilylmethyl triflate: Preparation and dipolar cycloaddition reactions of 1-(tert-butyldiphenylsilylmethyl)-6-cyano-4-methyl-1,2,5,6-tetrah ydropyridine

Synthetic Communications

Volumn 30, Issue 17, 2000, Pages 3203-3213

  Hart, David J ^a   Huang, Ying ^a  

^a OHIO STATE UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

1 (TERT BUTYLDIPHENYLSILYLMETHYL) 6 CYANO 4 METHYL 1,2,5,6 TETRAHYDROPYRIDINE; 3 PIPERIDEINE DERIVATIVE; MESYLIC ACID DERIVATIVE; PIPERIDINE DERIVATIVE; PYRIDINE DERIVATIVE; TERT BUTYLDIPHENYLSILYLMETHYL TRIFLATE; UNCLASSIFIED DRUG;

ALKYLATION; ARTICLE; CATALYSIS; CHEMICAL REACTION; CHEMICAL STRUCTURE; CYCLIZATION; REACTION ANALYSIS; REDUCTION; STOICHIOMETRY; SYNTHESIS;

EID: 0033852920     PISSN: 00397911     EISSN: None     Source Type: Journal    
DOI: 10.1080/00397910008086931     Document Type: Article

References (23)

1. Fry, E. M. J. Org. Chem. 1964, 29, 1647. Fry, E. M. and Beisler, J. A. J. Org. Chem. 1970, 35, 2809.
2. Fry, E. M. J. Org. Chem. 1964, 29, 1647. Fry, E. M. and Beisler, J. A. J. Org. Chem. 1970, 35, 2809.
3. Guerrier, L., Royer, J., Grierson, D. S. and Husson, H.-P. J. Am. Chem. Soc. 1983, 105, 7754. Bosch, J., Rubiralta, M. and Bolos, J. Tetrahedron 1987, 43, 391.
4. Guerrier, L., Royer, J., Grierson, D. S. and Husson, H.-P. J. Am. Chem. Soc. 1983, 105, 7754. Bosch, J., Rubiralta, M. and Bolos, J. Tetrahedron 1987, 43, 391.
5. This paper is abstracted in part from the Ph.D. Thesis of Y. Huang, The Ohio State University (1998).
6. For reviews of azomethine ylid cycloadditions see: Terao, Y., Aono, M. and Achiwa, K. Heterocycles 1988, 27, 981. Vedejs, E. and West, F. Chem. Rev. 1988, 941.
7. For reviews of azomethine ylid cycloadditions see: Terao, Y., Aono, M. and Achiwa, K. Heterocycles 1988, 27, 981. Vedejs, E. and West, F. Chem. Rev. 1988, 941.
8. Padwa, A. and Chen, Y.-Y. Tetrahedron Lett. 1983, 24, 3447. Parker, K. A., Cohen, I. D., Padwa, A. and Dent, W. Tetrahedron Lett. 1984, 25, 4917. Padwa, A., Chen, Y.-Y., Dent, W. and Nimmesgern, H. J. Org. Chem. 1985, 50, 4006. Terao, Y., Kotaki, H., Imai, N. and Achiwa, K. Chem. Pharm. Bull. 1985, 33, 896.
9. Padwa, A. and Chen, Y.-Y. Tetrahedron Lett. 1983, 24, 3447. Parker, K. A., Cohen, I. D., Padwa, A. and Dent, W. Tetrahedron Lett. 1984, 25, 4917. Padwa, A., Chen, Y.-Y., Dent, W. and Nimmesgern, H. J. Org. Chem. 1985, 50, 4006. Terao, Y., Kotaki, H., Imai, N. and Achiwa, K. Chem. Pharm. Bull. 1985, 33, 896.
10. Padwa, A. and Chen, Y.-Y. Tetrahedron Lett. 1983, 24, 3447. Parker, K. A., Cohen, I. D., Padwa, A. and Dent, W. Tetrahedron Lett. 1984, 25, 4917. Padwa, A., Chen, Y.-Y., Dent, W. and Nimmesgern, H. J. Org. Chem. 1985, 50, 4006. Terao, Y., Kotaki, H., Imai, N. and Achiwa, K. Chem. Pharm. Bull. 1985, 33, 896.
11. Padwa, A. and Chen, Y.-Y. Tetrahedron Lett. 1983, 24, 3447. Parker, K. A., Cohen, I. D., Padwa, A. and Dent, W. Tetrahedron Lett. 1984, 25, 4917. Padwa, A., Chen, Y.-Y., Dent, W. and Nimmesgern, H. J. Org. Chem. 1985, 50, 4006. Terao, Y., Kotaki, H., Imai, N. and Achiwa, K. Chem. Pharm. Bull. 1985, 33, 896.
12. For related entries to azomethine ylids see: Imai, N., Terao, Y., Achiwa, K. and Sekiya, M. Tetrahedron Lett. 1984, 25, 1579. Hosomi, A., Sakata, Y. and Sakurai, H. Chem. Lett. 1984, 1117. Terao, Y., Kotaki, H., Imai, N. and Achiwa, K. Chem. Pharm. Bull. 1985, 33, 2762. Vedejs, E. and Martinez, G. R. J. Am. Chem. Soc. 1980, 102, 7993.
13. For related entries to azomethine ylids see: Imai, N., Terao, Y., Achiwa, K. and Sekiya, M. Tetrahedron Lett. 1984, 25, 1579. Hosomi, A., Sakata, Y. and Sakurai, H. Chem. Lett. 1984, 1117. Terao, Y., Kotaki, H., Imai, N. and Achiwa, K. Chem. Pharm. Bull. 1985, 33, 2762. Vedejs, E. and Martinez, G. R. J. Am. Chem. Soc. 1980, 102, 7993.
14. For related entries to azomethine ylids see: Imai, N., Terao, Y., Achiwa, K. and Sekiya, M. Tetrahedron Lett. 1984, 25, 1579. Hosomi, A., Sakata, Y. and Sakurai, H. Chem. Lett. 1984, 1117. Terao, Y., Kotaki, H., Imai, N. and Achiwa, K. Chem. Pharm. Bull. 1985, 33, 2762. Vedejs, E. and Martinez, G. R. J. Am. Chem. Soc. 1980, 102, 7993.
15. For related entries to azomethine ylids see: Imai, N., Terao, Y., Achiwa, K. and Sekiya, M. Tetrahedron Lett. 1984, 25, 1579. Hosomi, A., Sakata, Y. and Sakurai, H. Chem. Lett. 1984, 1117. Terao, Y., Kotaki, H., Imai, N. and Achiwa, K. Chem. Pharm. Bull. 1985, 33, 2762. Vedejs, E. and Martinez, G. R. J. Am. Chem. Soc. 1980, 102, 7993.
16. Cuadrado, P., Gonzalez, A. M., Ganzalez, B. and Pulido, F. J. Synth. Commun. 1989, 19, 275.
17. 23NSi m/e 269.1600, found m/e 269.1591. This compound has been found to participate as a nucleophile in alkylation reactions with alkyl halides, N-acylation reactions with lactones, and imine-forming reactions with aldehydes (Strecker synthesis). Details are elaborated in the thesis cited in reference 3.
18. Bosch, J., Feliz, M. and Bennasar, M.-L. Tetrahedron 1984, 40, 1419. Rubiralta, M., Diez, A. and Bosch, J. Heterocycles 1988, 27, 785.
19. Bosch, J., Feliz, M. and Bennasar, M.-L. Tetrahedron 1984, 40, 1419. Rubiralta, M., Diez, A. and Bosch, J. Heterocycles 1988, 27, 785.
20. The pyridines used to prepare 15 and 17 were synthesized by treatment of 3-acetylpyridine with methyllithium and sodium borohydride, respectively.
21. Treatment of 12 with silver fluoride in the presence of tras-1,2-bis(phenylsulfonyl)ethylene also provided a 20% yield of a 1:1 mixture of diastereomeric cycloadducts derived from ylid 25. Less reactive dipolarophiles failed to give cycloadducts.
22. Procedures are provided for representative reactions and less detail for related reactions.
23. Alcohol 10 has been reported only as a minor product during the course of unrelated studies: Antonsen, O., Benneche, T. and Undheim, K. Acta Chim. Scand. 1992, 46, 757.