Novel anionic cyclization of N-aziridinylimines. An efficient route to carbocycles via consecutive carbon-carbon bond formation approach

Journal of the American Chemical Society

Volumn 121, Issue 22, 1999, Pages 5330-5331

  Kim, Sunggak ^a   Oh, Dong Hyun ^a   Yoon, Joo Yong ^a   Cheong, Jae Ho ^a  

^a Korea Advanced Institute of Science and Technology (KAIST)   (South Korea)

Author keywords

[No Author keywords available]

Indexed keywords

ALKENE; N AZIRIDINYLIMINE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL ANALYSIS; CHEMICAL COMPOSITION; CHEMICAL REACTION; CYCLIZATION; ISOMERISM; REACTION ANALYSIS;

EID: 0344223541     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja990022p     Document Type: Article

References (46)

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2. For recent reviews, see: (a) Thebtaranonth, C.; Thebtaranonth, Y. Cyclization Reactions; CRC Press: Boca Raton, FL, 1994; p 169 (b) Ho, T.-L. Tandem Organic Reactions; John Wiley & Sons: New York, 1992. (c) Hudlicky, T.; Price, J. D. Chem. Rev. 1989, 89, 1467.
3. For recent reviews, see: (a) Thebtaranonth, C.; Thebtaranonth, Y. Cyclization Reactions; CRC Press: Boca Raton, FL, 1994; p 169 (b) Ho, T.- L. Tandem Organic Reactions; John Wiley & Sons: New York, 1992. (c) Hudlicky, T.; Price, J. D. Chem. Rev. 1989, 89, 1467.
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19. For the sake of convenience, only anionic cyclization reactions are shown in eq 2. The formation of carbon-carbon bonds is indicated by solid lines. We thank Professor D. P. Curran for his suggestion in naming the formation of carbon-carbon bonds.
20. For selected examples on polyene cyclizations, see: (a) Cationic: Johnson, W. S.; Chen, Y.-Q.; Kellog, M. S. J. Am. Chem. Soc. 1983, 105, 6653. Corey, E. J.; Virgil, S. C. J. Am. Chem. Soc. 1991, 113, 4025. (b) Carbopalladation: Abelman, M. M.; Overman, L. E. J. Am. Chem. Soc. 1988, 110, 2328. Zhang, Y.; Wu, G-z.; Agnel, G.; Negishi, E-i. J. Am. Chem. Soc. 1990, 112, 8590. Trost, B. M.; Shi, Y. J. Am. Chem. Soc. 1991, 113, 701. (c) Radical: Begley, M. J.; Pattenden, G.; Smithies, A. J.; Walter, D. S. Tetrahedron Lett. 1994, 35, 2417. Chen, L.; Gill, G. B.; Pattenden, G. Tetrahedron Lett. 1994, 35, 2593.
21. For selected examples on polyene cyclizations, see: (a) Cationic: Johnson, W. S.; Chen, Y.-Q.; Kellog, M. S. J. Am. Chem. Soc. 1983, 105, 6653. Corey, E. J.; Virgil, S. C. J. Am. Chem. Soc. 1991, 113, 4025. (b) Carbopalladation: Abelman, M. M.; Overman, L. E. J. Am. Chem. Soc. 1988, 110, 2328. Zhang, Y.; Wu, G-z.; Agnel, G.; Negishi, E-i. J. Am. Chem. Soc. 1990, 112, 8590. Trost, B. M.; Shi, Y. J. Am. Chem. Soc. 1991, 113, 701. (c) Radical: Begley, M. J.; Pattenden, G.; Smithies, A. J.; Walter, D. S. Tetrahedron Lett. 1994, 35, 2417. Chen, L.; Gill, G. B.; Pattenden, G. Tetrahedron Lett. 1994, 35, 2593.
22. For selected examples on polyene cyclizations, see: (a) Cationic: Johnson, W. S.; Chen, Y.-Q.; Kellog, M. S. J. Am. Chem. Soc. 1983, 105, 6653. Corey, E. J.; Virgil, S. C. J. Am. Chem. Soc. 1991, 113, 4025. (b) Carbopalladation: Abelman, M. M.; Overman, L. E. J. Am. Chem. Soc. 1988, 110, 2328. Zhang, Y.; Wu, G-z.; Agnel, G.; Negishi, E-i. J. Am. Chem. Soc. 1990, 112, 8590. Trost, B. M.; Shi, Y. J. Am. Chem. Soc. 1991, 113, 701. (c) Radical: Begley, M. J.; Pattenden, G.; Smithies, A. J.; Walter, D. S. Tetrahedron Lett. 1994, 35, 2417. Chen, L.; Gill, G. B.; Pattenden, G. Tetrahedron Lett. 1994, 35, 2593.
23. For selected examples on polyene cyclizations, see: (a) Cationic: Johnson, W. S.; Chen, Y.-Q.; Kellog, M. S. J. Am. Chem. Soc. 1983, 105, 6653. Corey, E. J.; Virgil, S. C. J. Am. Chem. Soc. 1991, 113, 4025. (b) Carbopalladation: Abelman, M. M.; Overman, L. E. J. Am. Chem. Soc. 1988, 110, 2328. Zhang, Y.; Wu, G-z.; Agnel, G.; Negishi, E-i. J. Am. Chem. Soc. 1990, 112, 8590. Trost, B. M.; Shi, Y. J. Am. Chem. Soc. 1991, 113, 701. (c) Radical: Begley, M. J.; Pattenden, G.; Smithies, A. J.; Walter, D. S. Tetrahedron Lett. 1994, 35, 2417. Chen, L.; Gill, G. B.; Pattenden, G. Tetrahedron Lett. 1994, 35, 2593.
24. For selected examples on polyene cyclizations, see: (a) Cationic: Johnson, W. S.; Chen, Y.-Q.; Kellog, M. S. J. Am. Chem. Soc. 1983, 105, 6653. Corey, E. J.; Virgil, S. C. J. Am. Chem. Soc. 1991, 113, 4025. (b) Carbopalladation: Abelman, M. M.; Overman, L. E. J. Am. Chem. Soc. 1988, 110, 2328. Zhang, Y.; Wu, G-z.; Agnel, G.; Negishi, E-i. J. Am. Chem. Soc. 1990, 112, 8590. Trost, B. M.; Shi, Y. J. Am. Chem. Soc. 1991, 113, 701. (c) Radical: Begley, M. J.; Pattenden, G.; Smithies, A. J.; Walter, D. S. Tetrahedron Lett. 1994, 35, 2417. Chen, L.; Gill, G. B.; Pattenden, G. Tetrahedron Lett. 1994, 35, 2593.
25. For selected examples on polyene cyclizations, see: (a) Cationic: Johnson, W. S.; Chen, Y.-Q.; Kellog, M. S. J. Am. Chem. Soc. 1983, 105, 6653. Corey, E. J.; Virgil, S. C. J. Am. Chem. Soc. 1991, 113, 4025. (b) Carbopalladation: Abelman, M. M.; Overman, L. E. J. Am. Chem. Soc. 1988, 110, 2328. Zhang, Y.; Wu, G-z.; Agnel, G.; Negishi, E-i. J. Am. Chem. Soc. 1990, 112, 8590. Trost, B. M.; Shi, Y. J. Am. Chem. Soc. 1991, 113, 701. (c) Radical: Begley, M. J.; Pattenden, G.; Smithies, A. J.; Walter, D. S. Tetrahedron Lett. 1994, 35, 2417. Chen, L.; Gill, G. B.; Pattenden, G. Tetrahedron Lett. 1994, 35, 2593.
26. For selected examples on polyene cyclizations, see: (a) Cationic: Johnson, W. S.; Chen, Y.-Q.; Kellog, M. S. J. Am. Chem. Soc. 1983, 105, 6653. Corey, E. J.; Virgil, S. C. J. Am. Chem. Soc. 1991, 113, 4025. (b) Carbopalladation: Abelman, M. M.; Overman, L. E. J. Am. Chem. Soc. 1988, 110, 2328. Zhang, Y.; Wu, G-z.; Agnel, G.; Negishi, E-i. J. Am. Chem. Soc. 1990, 112, 8590. Trost, B. M.; Shi, Y. J. Am. Chem. Soc. 1991, 113, 701. (c) Radical: Begley, M. J.; Pattenden, G.; Smithies, A. J.; Walter, D. S. Tetrahedron Lett. 1994, 35, 2417. Chen, L.; Gill, G. B.; Pattenden, G. Tetrahedron Lett. 1994, 35, 2593.
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29. For previous reports on anionic reactions of N-aziridinylimines, see: (a) Leone, C. L.; Chamberlin, A. R. Tetrahedron Lett. 1991, 32, 1691. (b) Kim, S.; Cho, C. M.; Yoon, J.-Y. J. Org. Chem. 1996, 61, 6018. (c) Oishi, M.; Yamamoto, H. Synlett 1997, 191.
30. For previous reports on anionic reactions of N-aziridinylimines, see: (a) Leone, C. L.; Chamberlin, A. R. Tetrahedron Lett. 1991, 32, 1691. (b) Kim, S.; Cho, C. M.; Yoon, J.-Y. J. Org. Chem. 1996, 61, 6018. (c) Oishi, M.; Yamamoto, H. Synlett 1997, 191.
31. For previous reports on anionic reactions of N-aziridinylimines, see: (a) Leone, C. L.; Chamberlin, A. R. Tetrahedron Lett. 1991, 32, 1691. (b) Kim, S.; Cho, C. M.; Yoon, J.-Y. J. Org. Chem. 1996, 61, 6018. (c) Oishi, M.; Yamamoto, H. Synlett 1997, 191.
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34. For the use of tosylhydrazones as 1,1-dipoles, see: (a) Shapiro, R. H.; Gadek, T. J. Org. Chem. 1974, 39, 3418. (b) Vedejs, E.; Stolle, W. T. Tetrahedron Lett. 1977, 135. (c) Bertz, S. H. Tetrahedron Lett. 1980, 21, 3151.
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39. The ratio was determined by GC-MS. The cis-isomer (10b) was prepared by the known procedure (Felkin, H.; Umpleby, J. D.; Hagaman, E.; Wenkert, E. Tetrahedron Lett. 1972, 2285). Furthermore, 10b was converted into 11b to determine the ratio of 11a and 11b (see Supporting Information).
40. The use of 1.0 equiv of allylmagnesium bromide under the similar conditions gave a mixture of 11 (42%) and 12 (10%) along with the protonated form of 8 (27%).
41. Curran, D. P. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon Press: New York, 1991; Vol. 4, Chapter 4.2.
42. We have no clear answer why organometallic reagents would influence the stereochemical outcome of the cyclized products. Stereochemistry of the anionic cyclizations will be investigated in the near future.
43. The reason for the low efficiency of trapping the resulting anions is unclear at the present. Furthermore, we failed to trap alkyllithium 9 in THF with several electrophiles. Probably, alkyllithium 9 would destroy THF rapidly. Stanetty, P.; Mihovilovic, M. D. J. Org. Chem. 1997, 62, 1514.
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