A general synthetic route to 1-azabicyclo[m.n.0]alkenes via cyclisation based on α-sulfinyl carbanions

Organic and Biomolecular Chemistry

Volumn 1, Issue 20, 2003, Pages 3495-3497

  Pohmakotr, Manat ^a   Numechai, Pornthep ^a   Prateeptongkum, Saisuree ^a   Tuchinda, Patoomratana ^a   Reutrakul, Vichai ^a  

^a Mahidol University   (Thailand)

Author keywords

[No Author keywords available]

Indexed keywords

ADDITION REACTIONS; CHEMICAL BONDS; PURIFICATION; QUENCHING; SYNTHESIS (CHEMICAL);

NUCLEOPHILLIC ADDITION;

OLEFINS;

EID: 0142227212     PISSN: 14770520     EISSN: None     Source Type: Journal    
DOI: 10.1039/b308383g     Document Type: Article

References (30)

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2. For some recent syntheses of pyrrolizidines, see: H. Yodo, T. Egawa and K. Takabe, Tetrahedron Lett., 2003, 44, 1643; H. Hasegawa, H. Senboku, Y. Kajizuka, K. Orito and M. Tokuda, Tetrahedron, 2003, 59, 827; P. Renaud, C. Ollivier and P. Panchaud, Angew. Chem., Int. Ed., 2002, 41, 3460; M. T. Epperson and D. Y. Gin, Angew. Chem., Int. Ed., 2002, 41, 1778; S.-H. Kim, Y. Park, H. Choo and J. K. Cha, Tetrahedron Lett., 2002, 43, 6657.
3. For some recent syntheses of pyrrolizidines, see: H. Yodo, T. Egawa and K. Takabe, Tetrahedron Lett., 2003, 44, 1643; H. Hasegawa, H. Senboku, Y. Kajizuka, K. Orito and M. Tokuda, Tetrahedron, 2003, 59, 827; P. Renaud, C. Ollivier and P. Panchaud, Angew. Chem., Int. Ed., 2002, 41, 3460; M. T. Epperson and D. Y. Gin, Angew. Chem., Int. Ed., 2002, 41, 1778; S.-H. Kim, Y. Park, H. Choo and J. K. Cha, Tetrahedron Lett., 2002, 43, 6657.
4. For some recent syntheses of pyrrolizidines, see: H. Yodo, T. Egawa and K. Takabe, Tetrahedron Lett., 2003, 44, 1643; H. Hasegawa, H. Senboku, Y. Kajizuka, K. Orito and M. Tokuda, Tetrahedron, 2003, 59, 827; P. Renaud, C. Ollivier and P. Panchaud, Angew. Chem., Int. Ed., 2002, 41, 3460; M. T. Epperson and D. Y. Gin, Angew. Chem., Int. Ed., 2002, 41, 1778; S.-H. Kim, Y. Park, H. Choo and J. K. Cha, Tetrahedron Lett., 2002, 43, 6657.
5. For some recent syntheses of pyrrolizidines, see: H. Yodo, T. Egawa and K. Takabe, Tetrahedron Lett., 2003, 44, 1643; H. Hasegawa, H. Senboku, Y. Kajizuka, K. Orito and M. Tokuda, Tetrahedron, 2003, 59, 827; P. Renaud, C. Ollivier and P. Panchaud, Angew. Chem., Int. Ed., 2002, 41, 3460; M. T. Epperson and D. Y. Gin, Angew. Chem., Int. Ed., 2002, 41, 1778; S.-H. Kim, Y. Park, H. Choo and J. K. Cha, Tetrahedron Lett., 2002, 43, 6657.
6. For some recent syntheses of pyrrolizidines, see: H. Yodo, T. Egawa and K. Takabe, Tetrahedron Lett., 2003, 44, 1643; H. Hasegawa, H. Senboku, Y. Kajizuka, K. Orito and M. Tokuda, Tetrahedron, 2003, 59, 827; P. Renaud, C. Ollivier and P. Panchaud, Angew. Chem., Int. Ed., 2002, 41, 3460; M. T. Epperson and D. Y. Gin, Angew. Chem., Int. Ed., 2002, 41, 1778; S.-H. Kim, Y. Park, H. Choo and J. K. Cha, Tetrahedron Lett., 2002, 43, 6657.
7. For an updated review on indolizidine and quinolizidine alkaloids, see: J. P. Michael, Nat. Prod. Rep., 2001, 18, 520 and references cited therein.
8. For some recent syntheses of indolizidines and quinolizidines, see: D. Basavaiah and A. J. Rao, Chem. Commun., 2003, 604; Z.-X. Feng and W.-S. Zhou, Tetrahedron Lett., 2003, 44, 497; C.-K. Sha and C.-M. Chau, Tetrahedron Lett., 2003, 44, 499; N. Buschmann, A. Rückert and S. Blechert, J. Org. Chem., 2002, 67, 4325; A. R. de Faria, E. L. Salvador and C. R. D. Correia, J. Org. Chem., 2002, 67, 3651; K. L. Chandra, M. Chandrasekhar and V. K. Singh, J. Org. Chem., 2002, 67, 4630; H. Ovaa, C. Stapper, G. A. van der Marcl, H. S. Overkleeft, J. H. van Boom and S. Blechart, Tetrahedron, 2002, 58, 7503; T. G. Back and M. D. Hamilton, Org. Lett., 2002, 4, 1779; Y. Song, S. Okamoto and F. Sato, Tetrahedron Lett., 2002, 43, 8635; R. K. Dieter and R. Watson, Tetrahedron Lett., 2002, 43, 7725.
9. For some recent syntheses of indolizidines and quinolizidines, see: D. Basavaiah and A. J. Rao, Chem. Commun., 2003, 604; Z.-X. Feng and W.-S. Zhou, Tetrahedron Lett., 2003, 44, 497; C.-K. Sha and C.-M. Chau, Tetrahedron Lett., 2003, 44, 499; N. Buschmann, A. Rückert and S. Blechert, J. Org. Chem., 2002, 67, 4325; A. R. de Faria, E. L. Salvador and C. R. D. Correia, J. Org. Chem., 2002, 67, 3651; K. L. Chandra, M. Chandrasekhar and V. K. Singh, J. Org. Chem., 2002, 67, 4630; H. Ovaa, C. Stapper, G. A. van der Marcl, H. S. Overkleeft, J. H. van Boom and S. Blechart, Tetrahedron, 2002, 58, 7503; T. G. Back and M. D. Hamilton, Org. Lett., 2002, 4, 1779; Y. Song, S. Okamoto and F. Sato, Tetrahedron Lett., 2002, 43, 8635; R. K. Dieter and R. Watson, Tetrahedron Lett., 2002, 43, 7725.
10. For some recent syntheses of indolizidines and quinolizidines, see: D. Basavaiah and A. J. Rao, Chem. Commun., 2003, 604; Z.-X. Feng and W.-S. Zhou, Tetrahedron Lett., 2003, 44, 497; C.-K. Sha and C.-M. Chau, Tetrahedron Lett., 2003, 44, 499; N. Buschmann, A. Rückert and S. Blechert, J. Org. Chem., 2002, 67, 4325; A. R. de Faria, E. L. Salvador and C. R. D. Correia, J. Org. Chem., 2002, 67, 3651; K. L. Chandra, M. Chandrasekhar and V. K. Singh, J. Org. Chem., 2002, 67, 4630; H. Ovaa, C. Stapper, G. A. van der Marcl, H. S. Overkleeft, J. H. van Boom and S. Blechart, Tetrahedron, 2002, 58, 7503; T. G. Back and M. D. Hamilton, Org. Lett., 2002, 4, 1779; Y. Song, S. Okamoto and F. Sato, Tetrahedron Lett., 2002, 43, 8635; R. K. Dieter and R. Watson, Tetrahedron Lett., 2002, 43, 7725.
11. For some recent syntheses of indolizidines and quinolizidines, see: D. Basavaiah and A. J. Rao, Chem. Commun., 2003, 604; Z.-X. Feng and W.-S. Zhou, Tetrahedron Lett., 2003, 44, 497; C.-K. Sha and C.-M. Chau, Tetrahedron Lett., 2003, 44, 499; N. Buschmann, A. Rückert and S. Blechert, J. Org. Chem., 2002, 67, 4325; A. R. de Faria, E. L. Salvador and C. R. D. Correia, J. Org. Chem., 2002, 67, 3651; K. L. Chandra, M. Chandrasekhar and V. K. Singh, J. Org. Chem., 2002, 67, 4630; H. Ovaa, C. Stapper, G. A. van der Marcl, H. S. Overkleeft, J. H. van Boom and S. Blechart, Tetrahedron, 2002, 58, 7503; T. G. Back and M. D. Hamilton, Org. Lett., 2002, 4, 1779; Y. Song, S. Okamoto and F. Sato, Tetrahedron Lett., 2002, 43, 8635; R. K. Dieter and R. Watson, Tetrahedron Lett., 2002, 43, 7725.
12. For some recent syntheses of indolizidines and quinolizidines, see: D. Basavaiah and A. J. Rao, Chem. Commun., 2003, 604; Z.-X. Feng and W.-S. Zhou, Tetrahedron Lett., 2003, 44, 497; C.-K. Sha and C.-M. Chau, Tetrahedron Lett., 2003, 44, 499; N. Buschmann, A. Rückert and S. Blechert, J. Org. Chem., 2002, 67, 4325; A. R. de Faria, E. L. Salvador and C. R. D. Correia, J. Org. Chem., 2002, 67, 3651; K. L. Chandra, M. Chandrasekhar and V. K. Singh, J. Org. Chem., 2002, 67, 4630; H. Ovaa, C. Stapper, G. A. van der Marcl, H. S. Overkleeft, J. H. van Boom and S. Blechart, Tetrahedron, 2002, 58, 7503; T. G. Back and M. D. Hamilton, Org. Lett., 2002, 4, 1779; Y. Song, S. Okamoto and F. Sato, Tetrahedron Lett., 2002, 43, 8635; R. K. Dieter and R. Watson, Tetrahedron Lett., 2002, 43, 7725.
13. For some recent syntheses of indolizidines and quinolizidines, see: D. Basavaiah and A. J. Rao, Chem. Commun., 2003, 604; Z.-X. Feng and W.-S. Zhou, Tetrahedron Lett., 2003, 44, 497; C.-K. Sha and C.-M. Chau, Tetrahedron Lett., 2003, 44, 499; N. Buschmann, A. Rückert and S. Blechert, J. Org. Chem., 2002, 67, 4325; A. R. de Faria, E. L. Salvador and C. R. D. Correia, J. Org. Chem., 2002, 67, 3651; K. L. Chandra, M. Chandrasekhar and V. K. Singh, J. Org. Chem., 2002, 67, 4630; H. Ovaa, C. Stapper, G. A. van der Marcl, H. S. Overkleeft, J. H. van Boom and S. Blechart, Tetrahedron, 2002, 58, 7503; T. G. Back and M. D. Hamilton, Org. Lett., 2002, 4, 1779; Y. Song, S. Okamoto and F. Sato, Tetrahedron Lett., 2002, 43, 8635; R. K. Dieter and R. Watson, Tetrahedron Lett., 2002, 43, 7725.
14. For some recent syntheses of indolizidines and quinolizidines, see: D. Basavaiah and A. J. Rao, Chem. Commun., 2003, 604; Z.-X. Feng and W.-S. Zhou, Tetrahedron Lett., 2003, 44, 497; C.-K. Sha and C.-M. Chau, Tetrahedron Lett., 2003, 44, 499; N. Buschmann, A. Rückert and S. Blechert, J. Org. Chem., 2002, 67, 4325; A. R. de Faria, E. L. Salvador and C. R. D. Correia, J. Org. Chem., 2002, 67, 3651; K. L. Chandra, M. Chandrasekhar and V. K. Singh, J. Org. Chem., 2002, 67, 4630; H. Ovaa, C. Stapper, G. A. van der Marcl, H. S. Overkleeft, J. H. van Boom and S. Blechart, Tetrahedron, 2002, 58, 7503; T. G. Back and M. D. Hamilton, Org. Lett., 2002, 4, 1779; Y. Song, S. Okamoto and F. Sato, Tetrahedron Lett., 2002, 43, 8635; R. K. Dieter and R. Watson, Tetrahedron Lett., 2002, 43, 7725.
15. For some recent syntheses of indolizidines and quinolizidines, see: D. Basavaiah and A. J. Rao, Chem. Commun., 2003, 604; Z.-X. Feng and W.-S. Zhou, Tetrahedron Lett., 2003, 44, 497; C.-K. Sha and C.-M. Chau, Tetrahedron Lett., 2003, 44, 499; N. Buschmann, A. Rückert and S. Blechert, J. Org. Chem., 2002, 67, 4325; A. R. de Faria, E. L. Salvador and C. R. D. Correia, J. Org. Chem., 2002, 67, 3651; K. L. Chandra, M. Chandrasekhar and V. K. Singh, J. Org. Chem., 2002, 67, 4630; H. Ovaa, C. Stapper, G. A. van der Marcl, H. S. Overkleeft, J. H. van Boom and S. Blechart, Tetrahedron, 2002, 58, 7503; T. G. Back and M. D. Hamilton, Org. Lett., 2002, 4, 1779; Y. Song, S. Okamoto and F. Sato, Tetrahedron Lett., 2002, 43, 8635; R. K. Dieter and R. Watson, Tetrahedron Lett., 2002, 43, 7725.
16. For some recent syntheses of indolizidines and quinolizidines, see: D. Basavaiah and A. J. Rao, Chem. Commun., 2003, 604; Z.-X. Feng and W.-S. Zhou, Tetrahedron Lett., 2003, 44, 497; C.-K. Sha and C.-M. Chau, Tetrahedron Lett., 2003, 44, 499; N. Buschmann, A. Rückert and S. Blechert, J. Org. Chem., 2002, 67, 4325; A. R. de Faria, E. L. Salvador and C. R. D. Correia, J. Org. Chem., 2002, 67, 3651; K. L. Chandra, M. Chandrasekhar and V. K. Singh, J. Org. Chem., 2002, 67, 4630; H. Ovaa, C. Stapper, G. A. van der Marcl, H. S. Overkleeft, J. H. van Boom and S. Blechart, Tetrahedron, 2002, 58, 7503; T. G. Back and M. D. Hamilton, Org. Lett., 2002, 4, 1779; Y. Song, S. Okamoto and F. Sato, Tetrahedron Lett., 2002, 43, 8635; R. K. Dieter and R. Watson, Tetrahedron Lett., 2002, 43, 7725.
17. For some recent syntheses of indolizidines and quinolizidines, see: D. Basavaiah and A. J. Rao, Chem. Commun., 2003, 604; Z.-X. Feng and W.-S. Zhou, Tetrahedron Lett., 2003, 44, 497; C.-K. Sha and C.-M. Chau, Tetrahedron Lett., 2003, 44, 499; N. Buschmann, A. Rückert and S. Blechert, J. Org. Chem., 2002, 67, 4325; A. R. de Faria, E. L. Salvador and C. R. D. Correia, J. Org. Chem., 2002, 67, 3651; K. L. Chandra, M. Chandrasekhar and V. K. Singh, J. Org. Chem., 2002, 67, 4630; H. Ovaa, C. Stapper, G. A. van der Marcl, H. S. Overkleeft, J. H. van Boom and S. Blechart, Tetrahedron, 2002, 58, 7503; T. G. Back and M. D. Hamilton, Org. Lett., 2002, 4, 1779; Y. Song, S. Okamoto and F. Sato, Tetrahedron Lett., 2002, 43, 8635; R. K. Dieter and R. Watson, Tetrahedron Lett., 2002, 43, 7725.
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19. P. Wipf, Y. Kim and D. M. Goldstein, J. Am. Chem. Soc., 1995, 117, 11106; D. M. Goldstein and P. Wipf, Tetrahedron Lett., 1996, 37, 739.
20. For examples of general synthetic routes to 1-azabicyclo[5.4.0]- and [5.3.0]-alkanes, see: W. H. Pearson, D. A. Hutta and W. K. Fang, J. Org. Chem., 2000, 65, 8326; W. H. Pearson and W. K. Fang, J. Org. Chem., 2000, 65, 7158; A. Kinoshita and M. Mori, J. Org. Chem., 1996, 61, 8356; K. Kiewel, M. Tallant and G A. Sulikowski, Tetrahedron Lett., 2001, 42, 6621; S. L. Lim, S. Ma and P. Beak, J. Org. Chem., 2001, 66, 9056.
21. For examples of general synthetic routes to 1-azabicyclo[5.4.0]- and [5.3.0]-alkanes, see: W. H. Pearson, D. A. Hutta and W. K. Fang, J. Org. Chem., 2000, 65, 8326; W. H. Pearson and W. K. Fang, J. Org. Chem., 2000, 65, 7158; A. Kinoshita and M. Mori, J. Org. Chem., 1996, 61, 8356; K. Kiewel, M. Tallant and G A. Sulikowski, Tetrahedron Lett., 2001, 42, 6621; S. L. Lim, S. Ma and P. Beak, J. Org. Chem., 2001, 66, 9056.
22. For examples of general synthetic routes to 1-azabicyclo[5.4.0]- and [5.3.0]-alkanes, see: W. H. Pearson, D. A. Hutta and W. K. Fang, J. Org. Chem., 2000, 65, 8326; W. H. Pearson and W. K. Fang, J. Org. Chem., 2000, 65, 7158; A. Kinoshita and M. Mori, J. Org. Chem., 1996, 61, 8356; K. Kiewel, M. Tallant and G A. Sulikowski, Tetrahedron Lett., 2001, 42, 6621; S. L. Lim, S. Ma and P. Beak, J. Org. Chem., 2001, 66, 9056.
23. For examples of general synthetic routes to 1-azabicyclo[5.4.0]- and [5.3.0]-alkanes, see: W. H. Pearson, D. A. Hutta and W. K. Fang, J. Org. Chem., 2000, 65, 8326; W. H. Pearson and W. K. Fang, J. Org. Chem., 2000, 65, 7158; A. Kinoshita and M. Mori, J. Org. Chem., 1996, 61, 8356; K. Kiewel, M. Tallant and G A. Sulikowski, Tetrahedron Lett., 2001, 42, 6621; S. L. Lim, S. Ma and P. Beak, J. Org. Chem., 2001, 66, 9056.
24. For examples of general synthetic routes to 1-azabicyclo[5.4.0]- and [5.3.0]-alkanes, see: W. H. Pearson, D. A. Hutta and W. K. Fang, J. Org. Chem., 2000, 65, 8326; W. H. Pearson and W. K. Fang, J. Org. Chem., 2000, 65, 7158; A. Kinoshita and M. Mori, J. Org. Chem., 1996, 61, 8356; K. Kiewel, M. Tallant and G A. Sulikowski, Tetrahedron Lett., 2001, 42, 6621; S. L. Lim, S. Ma and P. Beak, J. Org. Chem., 2001, 66, 9056.
25. M. Pohmakotr and S. Chancharunee, Tetrahedron Lett., 1984, 25, 4141; M. Pohmakotr and S. Popaung, Tetrahedron Lett., 1988, 29, 4189; M. Pohmakotr, S. Popaung and S. Chancharunee, Tetrahedron Lett., 1990, 31, 3783; M. Pohmakotr, T. Junpirom, S. Popaung, P. Tuchinda and V. Reutrakul, Tetrahedron Lett., 2002, 43, 7385.
26. M. Pohmakotr and S. Chancharunee, Tetrahedron Lett., 1984, 25, 4141; M. Pohmakotr and S. Popaung, Tetrahedron Lett., 1988, 29, 4189; M. Pohmakotr, S. Popaung and S. Chancharunee, Tetrahedron Lett., 1990, 31, 3783; M. Pohmakotr, T. Junpirom, S. Popaung, P. Tuchinda and V. Reutrakul, Tetrahedron Lett., 2002, 43, 7385.
27. M. Pohmakotr and S. Chancharunee, Tetrahedron Lett., 1984, 25, 4141; M. Pohmakotr and S. Popaung, Tetrahedron Lett., 1988, 29, 4189; M. Pohmakotr, S. Popaung and S. Chancharunee, Tetrahedron Lett., 1990, 31, 3783; M. Pohmakotr, T. Junpirom, S. Popaung, P. Tuchinda and V. Reutrakul, Tetrahedron Lett., 2002, 43, 7385.
28. M. Pohmakotr and S. Chancharunee, Tetrahedron Lett., 1984, 25, 4141; M. Pohmakotr and S. Popaung, Tetrahedron Lett., 1988, 29, 4189; M. Pohmakotr, S. Popaung and S. Chancharunee, Tetrahedron Lett., 1990, 31, 3783; M. Pohmakotr, T. Junpirom, S. Popaung, P. Tuchinda and V. Reutrakul, Tetrahedron Lett., 2002, 43, 7385.
29. A compound of type Sa was demonstrated by D. H. Hua and coworkers to be a versatile precursor for the synthesis of elaeokanine A and elaeokanine B: D. H. Hua, S. N. Bharathi, P. D. Robinson and A. Tsujimoto, J. Org. Chem., 1990, 55, 2128.
30. + + 1, 3%), 231 (4%), 199 (67%), 170 (51%), 120 (100%), 108 (6%), 92 (8%), 80 (5%), 77 (4%), 65 (5%).