Synthesis of 3-hydroxy and 3-amino 2-substituted n-heterocycles via enamine oxidation and aziridination

Tetrahedron Letters

Volumn 39, Issue 48, 1998, Pages 8885-8888

  Sunose, Mihiro ^a   Anderson, Kirsty M ^a   Orpen, A Guy ^a   Gallagher, Timothy ^a   Macdonald, Simon J F ^b  

^a UNIVERSITY OF BRISTOL   (United Kingdom)

^b GLAXOSMITHKLINE   (United Kingdom)

Author keywords

Asymmetric dihydroxylation; Asymmetric epoxidation; Aziridines; Enamines

Indexed keywords

AZIRIDINE DERIVATIVE; ENAMINE; HETEROCYCLIC AMINE; MANGANESE; PIPERIDINE DERIVATIVE; PROTEINASE INHIBITOR; PYRROLIDINE DERIVATIVE;

AMINATION; ARTICLE; CONTROLLED STUDY; DRUG SYNTHESIS; EPOXIDATION; HYDROXYLATION; OXIDATION;

EID: 0032569868     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(98)01915-7     Document Type: Article

References (25)

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2. Shono, T.; Matsumura, Y.; Onomura, O.; Ogaki, M.; Kanazawa, T.; J. Org. Chem. 1987; 52, 536. Nilsson, K.; Hallberg, A. J. Org. Chem. 1990, 55, 2464. Van Broeck, P. I.; Van Doren, P. E.; Toppet, S. M.; Hoornaert, G. J. J. Chem. Soc. Perkin Trans.1 1992, 415. Ozawa, F.; Hayashi, T. J. Organomet. Chem. 1992, 428, 267. de Faria, A. R.; Matos, C. R. R.; Correia, C. R. D. Tetrahedron Lett. 1993, 34, 27. Grotjahn, D. B.; Vollhardt, K. P. C. Synthesis 1993; 579.
3. Shono, T.; Matsumura, Y.; Onomura, O.; Ogaki, M.; Kanazawa, T.; J. Org. Chem. 1987; 52, 536. Nilsson, K.; Hallberg, A. J. Org. Chem. 1990, 55, 2464. Van Broeck, P. I.; Van Doren, P. E.; Toppet, S. M.; Hoornaert, G. J. J. Chem. Soc. Perkin Trans.1 1992, 415. Ozawa, F.; Hayashi, T. J. Organomet. Chem. 1992, 428, 267. de Faria, A. R.; Matos, C. R. R.; Correia, C. R. D. Tetrahedron Lett. 1993, 34, 27. Grotjahn, D. B.; Vollhardt, K. P. C. Synthesis 1993; 579.
4. Shono, T.; Matsumura, Y.; Onomura, O.; Ogaki, M.; Kanazawa, T.; J. Org. Chem. 1987; 52, 536. Nilsson, K.; Hallberg, A. J. Org. Chem. 1990, 55, 2464. Van Broeck, P. I.; Van Doren, P. E.; Toppet, S. M.; Hoornaert, G. J. J. Chem. Soc. Perkin Trans.1 1992, 415. Ozawa, F.; Hayashi, T. J. Organomet. Chem. 1992, 428, 267. de Faria, A. R.; Matos, C. R. R.; Correia, C. R. D. Tetrahedron Lett. 1993, 34, 27. Grotjahn, D. B.; Vollhardt, K. P. C. Synthesis 1993; 579.
5. Shono, T.; Matsumura, Y.; Onomura, O.; Ogaki, M.; Kanazawa, T.; J. Org. Chem. 1987; 52, 536. Nilsson, K.; Hallberg, A. J. Org. Chem. 1990, 55, 2464. Van Broeck, P. I.; Van Doren, P. E.; Toppet, S. M.; Hoornaert, G. J. J. Chem. Soc. Perkin Trans.1 1992, 415. Ozawa, F.; Hayashi, T. J. Organomet. Chem. 1992, 428, 267. de Faria, A. R.; Matos, C. R. R.; Correia, C. R. D. Tetrahedron Lett. 1993, 34, 27. Grotjahn, D. B.; Vollhardt, K. P. C. Synthesis 1993; 579.
6. Shono, T.; Matsumura, Y.; Onomura, O.; Ogaki, M.; Kanazawa, T.; J. Org. Chem. 1987; 52, 536. Nilsson, K.; Hallberg, A. J. Org. Chem. 1990, 55, 2464. Van Broeck, P. I.; Van Doren, P. E.; Toppet, S. M.; Hoornaert, G. J. J. Chem. Soc. Perkin Trans.1 1992, 415. Ozawa, F.; Hayashi, T. J. Organomet. Chem. 1992, 428, 267. de Faria, A. R.; Matos, C. R. R.; Correia, C. R. D. Tetrahedron Lett. 1993, 34, 27. Grotjahn, D. B.; Vollhardt, K. P. C. Synthesis 1993; 579.
7. 2. The oxidation of enamines with dimethyl dioxirane has been reported: Burgess, L. E.; Gross, E. K. M.; Jurka, J. Tetrahedron Lett. 1996, 37, 3255. Electrochemical oxidation has also been described: Matsumura, Y.; Takeshima, Y.; Okita, H. Bull. Chem. Soc. Jpn. 1994, 67, 304.
8. 2. The oxidation of enamines with dimethyl dioxirane has been reported: Burgess, L. E.; Gross, E. K. M.; Jurka, J. Tetrahedron Lett. 1996, 37, 3255. Electrochemical oxidation has also been described: Matsumura, Y.; Takeshima, Y.; Okita, H. Bull. Chem. Soc. Jpn. 1994, 67, 304.
9. 3. Sugisaki, C. H.; Carroll, P. J.; Correia, C. R. D. Tetrahedron Lett. 1998, 39, 3413. These authors indicate that different levels of asymmetric induction were associated with the cis and trans diol derivatives.
10. 4. Palucki, M.; Pospisil, P. J.; Zhang, W.; J.; Jacobsen, E. N. J. Am. Chem. Soc. 1994, 116, 9333. Palucki, M.; McCormick, G. J.; Jacobsen, E. N. Tetrahedron Lett. 1995, 36, 5457. Jacobsen, E. N. In Comprehensive Organometallic Chemistry II, Abel, E. W.; Stone, F. G. A.; Wilktnson, G., eds.; Pergamon: New York, 1996 Vol. 12, pp. 1097-1135.
11. 4. Palucki, M.; Pospisil, P. J.; Zhang, W.; J.; Jacobsen, E. N. J. Am. Chem. Soc. 1994, 116, 9333. Palucki, M.; McCormick, G. J.; Jacobsen, E. N. Tetrahedron Lett. 1995, 36, 5457. Jacobsen, E. N. In Comprehensive Organometallic Chemistry II, Abel, E. W.; Stone, F. G. A.; Wilktnson, G., eds.; Pergamon: New York, 1996 Vol. 12, pp. 1097-1135.
12. 4. Palucki, M.; Pospisil, P. J.; Zhang, W.; J.; Jacobsen, E. N. J. Am. Chem. Soc. 1994, 116, 9333. Palucki, M.; McCormick, G. J.; Jacobsen, E. N. Tetrahedron Lett. 1995, 36, 5457. Jacobsen, E. N. In Comprehensive Organometallic Chemistry II, Abel, E. W.; Stone, F. G. A.; Wilktnson, G., eds.; Pergamon: New York, 1996 Vol. 12, pp. 1097-1135.
13. 5. The cis and trans isomers of (2a) could not be separated and were analysed as the mixture. The isomers of (2b) were separated prior to conversion to the corresponding Mosher esters, and in both series the corresponding racemates were prepared and used as standards.
14. 6. Sharpless, K. B.; Amberg, W.; Bennani, Y. L.; Crispino, G. A.; Hartung, J.; Jeong, K.-S.; Kwong, H.-L.; Morikawa, K.; Wang, Z.-M.; Xu, D.; Zhang, X.-L. J. Org. Chem. 1992, 57, 2768. Kolb, H. C.; VanNieuwenhze, M. S.; Sharpless, K. B. Chem. Rev. 1994, 94, 2483.
15. 6. Sharpless, K. B.; Amberg, W.; Bennani, Y. L.; Crispino, G. A.; Hartung, J.; Jeong, K.-S.; Kwong, H.-L.; Morikawa, K.; Wang, Z.-M.; Xu, D.; Zhang, X.-L. J. Org. Chem. 1992, 57, 2768. Kolb, H. C.; VanNieuwenhze, M. S.; Sharpless, K. B. Chem. Rev. 1994, 94, 2483.
16. 7. Asymmetric aminohydroxylation of silyl enol ethers, see Phukan, P.; Sudalai, A. Tetrahedron: Asymmetry, 1998, 9, 1001.
17. 8. Li, G.; Chang, H.-T. Sharpless, K. B. Angew. Chem. Int, Ed. Engl. 1996, 35, 451.
18. 9. Du Bois, J.; Hong, J.; Carreira, E. M.; Day, M. W. J. Am. Chem. Soc. 1996, 118, 915. Du Bois, J.; Tomooka, C. S.; Hong, J.; Carreira, E. M. J. Am. Chem. Soc. 1997, 119, 3179. Du Bois, J.; Tomooka, C. S.; Hong, J.; Carreira, E. M. Acc. Chem. Res. 1997, 30, 364. See also Groves, J. T.; Takahashi, T. J. Am. Chem. Soc. 1983, 105, 2073.
19. 9. Du Bois, J.; Hong, J.; Carreira, E. M.; Day, M. W. J. Am. Chem. Soc. 1996, 118, 915. Du Bois, J.; Tomooka, C. S.; Hong, J.; Carreira, E. M. J. Am. Chem. Soc. 1997, 119, 3179. Du Bois, J.; Tomooka, C. S.; Hong, J.; Carreira, E. M. Acc. Chem. Res. 1997, 30, 364. See also Groves, J. T.; Takahashi, T. J. Am. Chem. Soc. 1983, 105, 2073.
20. 9. Du Bois, J.; Hong, J.; Carreira, E. M.; Day, M. W. J. Am. Chem. Soc. 1996, 118, 915. Du Bois, J.; Tomooka, C. S.; Hong, J.; Carreira, E. M. J. Am. Chem. Soc. 1997, 119, 3179. Du Bois, J.; Tomooka, C. S.; Hong, J.; Carreira, E. M. Acc. Chem. Res. 1997, 30, 364. See also Groves, J. T.; Takahashi, T. J. Am. Chem. Soc. 1983, 105, 2073.
21. 9. Du Bois, J.; Hong, J.; Carreira, E. M.; Day, M. W. J. Am. Chem. Soc. 1996, 118, 915. Du Bois, J.; Tomooka, C. S.; Hong, J.; Carreira, E. M. J. Am. Chem. Soc. 1997, 119, 3179. Du Bois, J.; Tomooka, C. S.; Hong, J.; Carreira, E. M. Acc. Chem. Res. 1997, 30, 364. See also Groves, J. T.; Takahashi, T. J. Am. Chem. Soc. 1983, 105, 2073.
22. 1 = 0.044.
23. 2 at -78 °C, then warming to 0 °C (over 2h). The mixture was then re-cooled to -78 °C and (1a) was added (over 2h via syringe pump) and the mixture was then warmed to r.t. over 4h, after which time McOH(D) was added. Interestingly, when both "normal" and "aged" reactions were monitored by TLC, (8) and (9) were the major components observed. However, when these reactions were subsequently quenched with MeOD, (6) and (7) isolated contained no incorporation of deuterium at C(3). This suggests (i) that (9) is not involved in the pathway leading to (6/7) (although the species present in solution appears to break down to (9) on TLC), (ii) the "aged" reagent is quite distinct to that produced under "normal" conditions and (iii) that two discreet animation pathways are available. We have been unsuccessful in converting (9) to (6/7) using MeOH and PyHTs (pyridinium tosylate) but thermolysis (PhMe, PyHTs, 100°C) of (7) gave (9) (20%) together with (6) (30%) and recovered (7) (15%).
24. 12. The trans lactam-based protease inhibitors were discovered by GlaxoWcllcome: Macdonald, S. J. F.; Belton, D. J.; Spooner, J. E.; Anson, M. S.; Harrison, L. A.; Mills, K.; Upton, R, J.; Dowle, M. D.; Smith, R. A.; Molloy, C.; Risley, C. J. Med Chem. in press.
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