An expedient phosphine-catalyzed [4 + 2] annulation: Synthesis of highly functionalized tetrahydropyridines

Journal of the American Chemical Society

Volumn 125, Issue 16, 2003, Pages 4716-4717

  Zhu, Xue Feng ^a   Lan, Jie ^a   Kwon, Ohyun ^a  

^a UNIVERSITY OF CALIFORNIA   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

PHOSPHINE; PYRIDINE DERIVATIVE; TETRAHYDROPYRIDINE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CATALYSIS; CHEMICAL REACTION; CYCLOADDITION; DIASTEREOISOMER; DIELS ALDER REACTION; PROTON TRANSPORT; REACTION ANALYSIS; STEREOCHEMISTRY; SYNTHESIS;

BUTADIENES; CATALYSIS; CYCLIZATION; IMINES; PHOSPHINES; PYRIDINES; TOSYL COMPOUNDS;

EID: 0037462076     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja0344009     Document Type: Article

References (35)

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7. To our knowledge there are 13 examples of 1,4-dipoles/1,4-dipole equivalents that undergo the (formal) [4 + 2] cycloadditions. For selected references, see: (a) Huisgen, R. In Topics in Heterocyclic Chemistry; Castle, R., Ed.; John Wiley & Sons: New York, 1969; Chapter 8. (b) Shair, M. D.; Yoon, T. Y.; Mosny, K. K.; Chou, T. C.; Danishefsky, S. J. J. Am. Chem. Soc. 1996, 118, 9509-9525. (c) Padwa, A.; Harring, S. R.; Semones, M. A. J. Org. Chem. 1998, 63, 44-54 and references therein. (d) Rigby, J. H. Synlett 2000, 1-12 and references therein.
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17. Unpublished results from our laboratory.
18. For a review, see: (a) Lu, X.; Zhang, C.; Xu, Z. Acc. Chem. Res. 2001, 34, 535-544. For selected recent reports on phosphine-catalyzed reactions, see: (b) Kuroda, H.; Tomita, I.; Endo, T. Org. Lett. 2003, 5, 129-131. (c) Lu, C.; Lu, X. Org. Lett. 2002, 4, 4677-4679. (d) Du, Y.; Lu, X.; Yu, Y. J. Org. Chem. 2002, 67, 8901-8905. (e) Lu, B.; Davis, R.; Joshi, B.; Reynolds, D. W. J. Org. Chem. 2002, 67, 4595-4598. (f) Frank, S. A.; Mergott, D. J.; Roush, W. R. J. Am. Chem. Soc. 2002, 124, 2404-2405. (g) Wang, L.-C.; Luis, A. L.; Agapiou, K.; Krische, M. J. J. Am. Chem. Soc. 2002, 124, 2402-2403. (h) Trost, B. M.; Dake, G. R. J. Am. Chem. Soc. 1997, 119, 7595-7596. (i) Zhu, G.; Chen, Z.; Jiang, Q.; Xiao, D.; Cao, P.; Zhang, X. J. Am. Chem. Soc. 1997, 119, 3836-3837.
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20. For a review, see: (a) Lu, X.; Zhang, C.; Xu, Z. Acc. Chem. Res. 2001, 34, 535-544. For selected recent reports on phosphine-catalyzed reactions, see: (b) Kuroda, H.; Tomita, I.; Endo, T. Org. Lett. 2003, 5, 129-131. (c) Lu, C.; Lu, X. Org. Lett. 2002, 4, 4677-4679. (d) Du, Y.; Lu, X.; Yu, Y. J. Org. Chem. 2002, 67, 8901-8905. (e) Lu, B.; Davis, R.; Joshi, B.; Reynolds, D. W. J. Org. Chem. 2002, 67, 4595-4598. (f) Frank, S. A.; Mergott, D. J.; Roush, W. R. J. Am. Chem. Soc. 2002, 124, 2404-2405. (g) Wang, L.-C.; Luis, A. L.; Agapiou, K.; Krische, M. J. J. Am. Chem. Soc. 2002, 124, 2402-2403. (h) Trost, B. M.; Dake, G. R. J. Am. Chem. Soc. 1997, 119, 7595-7596. (i) Zhu, G.; Chen, Z.; Jiang, Q.; Xiao, D.; Cao, P.; Zhang, X. J. Am. Chem. Soc. 1997, 119, 3836-3837.
21. For a review, see: (a) Lu, X.; Zhang, C.; Xu, Z. Acc. Chem. Res. 2001, 34, 535-544. For selected recent reports on phosphine-catalyzed reactions, see: (b) Kuroda, H.; Tomita, I.; Endo, T. Org. Lett. 2003, 5, 129-131. (c) Lu, C.; Lu, X. Org. Lett. 2002, 4, 4677-4679. (d) Du, Y.; Lu, X.; Yu, Y. J. Org. Chem. 2002, 67, 8901-8905. (e) Lu, B.; Davis, R.; Joshi, B.; Reynolds, D. W. J. Org. Chem. 2002, 67, 4595-4598. (f) Frank, S. A.; Mergott, D. J.; Roush, W. R. J. Am. Chem. Soc. 2002, 124, 2404-2405. (g) Wang, L.-C.; Luis, A. L.; Agapiou, K.; Krische, M. J. J. Am. Chem. Soc. 2002, 124, 2402-2403. (h) Trost, B. M.; Dake, G. R. J. Am. Chem. Soc. 1997, 119, 7595-7596. (i) Zhu, G.; Chen, Z.; Jiang, Q.; Xiao, D.; Cao, P.; Zhang, X. J. Am. Chem. Soc. 1997, 119, 3836-3837.
22. For a review, see: (a) Lu, X.; Zhang, C.; Xu, Z. Acc. Chem. Res. 2001, 34, 535-544. For selected recent reports on phosphine-catalyzed reactions, see: (b) Kuroda, H.; Tomita, I.; Endo, T. Org. Lett. 2003, 5, 129-131. (c) Lu, C.; Lu, X. Org. Lett. 2002, 4, 4677-4679. (d) Du, Y.; Lu, X.; Yu, Y. J. Org. Chem. 2002, 67, 8901-8905. (e) Lu, B.; Davis, R.; Joshi, B.; Reynolds, D. W. J. Org. Chem. 2002, 67, 4595-4598. (f) Frank, S. A.; Mergott, D. J.; Roush, W. R. J. Am. Chem. Soc. 2002, 124, 2404-2405. (g) Wang, L.-C.; Luis, A. L.; Agapiou, K.; Krische, M. J. J. Am. Chem. Soc. 2002, 124, 2402-2403. (h) Trost, B. M.; Dake, G. R. J. Am. Chem. Soc. 1997, 119, 7595-7596. (i) Zhu, G.; Chen, Z.; Jiang, Q.; Xiao, D.; Cao, P.; Zhang, X. J. Am. Chem. Soc. 1997, 119, 3836-3837.
23. For a review, see: (a) Lu, X.; Zhang, C.; Xu, Z. Acc. Chem. Res. 2001, 34, 535-544. For selected recent reports on phosphine-catalyzed reactions, see: (b) Kuroda, H.; Tomita, I.; Endo, T. Org. Lett. 2003, 5, 129-131. (c) Lu, C.; Lu, X. Org. Lett. 2002, 4, 4677-4679. (d) Du, Y.; Lu, X.; Yu, Y. J. Org. Chem. 2002, 67, 8901-8905. (e) Lu, B.; Davis, R.; Joshi, B.; Reynolds, D. W. J. Org. Chem. 2002, 67, 4595-4598. (f) Frank, S. A.; Mergott, D. J.; Roush, W. R. J. Am. Chem. Soc. 2002, 124, 2404-2405. (g) Wang, L.-C.; Luis, A. L.; Agapiou, K.; Krische, M. J. J. Am. Chem. Soc. 2002, 124, 2402-2403. (h) Trost, B. M.; Dake, G. R. J. Am. Chem. Soc. 1997, 119, 7595-7596. (i) Zhu, G.; Chen, Z.; Jiang, Q.; Xiao, D.; Cao, P.; Zhang, X. J. Am. Chem. Soc. 1997, 119, 3836-3837.
24. For a review, see: (a) Lu, X.; Zhang, C.; Xu, Z. Acc. Chem. Res. 2001, 34, 535-544. For selected recent reports on phosphine-catalyzed reactions, see: (b) Kuroda, H.; Tomita, I.; Endo, T. Org. Lett. 2003, 5, 129-131. (c) Lu, C.; Lu, X. Org. Lett. 2002, 4, 4677-4679. (d) Du, Y.; Lu, X.; Yu, Y. J. Org. Chem. 2002, 67, 8901-8905. (e) Lu, B.; Davis, R.; Joshi, B.; Reynolds, D. W. J. Org. Chem. 2002, 67, 4595-4598. (f) Frank, S. A.; Mergott, D. J.; Roush, W. R. J. Am. Chem. Soc. 2002, 124, 2404-2405. (g) Wang, L.-C.; Luis, A. L.; Agapiou, K.; Krische, M. J. J. Am. Chem. Soc. 2002, 124, 2402-2403. (h) Trost, B. M.; Dake, G. R. J. Am. Chem. Soc. 1997, 119, 7595-7596. (i) Zhu, G.; Chen, Z.; Jiang, Q.; Xiao, D.; Cao, P.; Zhang, X. J. Am. Chem. Soc. 1997, 119, 3836-3837.
25. For a review, see: (a) Lu, X.; Zhang, C.; Xu, Z. Acc. Chem. Res. 2001, 34, 535-544. For selected recent reports on phosphine-catalyzed reactions, see: (b) Kuroda, H.; Tomita, I.; Endo, T. Org. Lett. 2003, 5, 129-131. (c) Lu, C.; Lu, X. Org. Lett. 2002, 4, 4677-4679. (d) Du, Y.; Lu, X.; Yu, Y. J. Org. Chem. 2002, 67, 8901-8905. (e) Lu, B.; Davis, R.; Joshi, B.; Reynolds, D. W. J. Org. Chem. 2002, 67, 4595-4598. (f) Frank, S. A.; Mergott, D. J.; Roush, W. R. J. Am. Chem. Soc. 2002, 124, 2404-2405. (g) Wang, L.-C.; Luis, A. L.; Agapiou, K.; Krische, M. J. J. Am. Chem. Soc. 2002, 124, 2402-2403. (h) Trost, B. M.; Dake, G. R. J. Am. Chem. Soc. 1997, 119, 7595-7596. (i) Zhu, G.; Chen, Z.; Jiang, Q.; Xiao, D.; Cao, P.; Zhang, X. J. Am. Chem. Soc. 1997, 119, 3836-3837.
26. For a review, see: (a) Lu, X.; Zhang, C.; Xu, Z. Acc. Chem. Res. 2001, 34, 535-544. For selected recent reports on phosphine-catalyzed reactions, see: (b) Kuroda, H.; Tomita, I.; Endo, T. Org. Lett. 2003, 5, 129-131. (c) Lu, C.; Lu, X. Org. Lett. 2002, 4, 4677-4679. (d) Du, Y.; Lu, X.; Yu, Y. J. Org. Chem. 2002, 67, 8901-8905. (e) Lu, B.; Davis, R.; Joshi, B.; Reynolds, D. W. J. Org. Chem. 2002, 67, 4595-4598. (f) Frank, S. A.; Mergott, D. J.; Roush, W. R. J. Am. Chem. Soc. 2002, 124, 2404-2405. (g) Wang, L.-C.; Luis, A. L.; Agapiou, K.; Krische, M. J. J. Am. Chem. Soc. 2002, 124, 2402-2403. (h) Trost, B. M.; Dake, G. R. J. Am. Chem. Soc. 1997, 119, 7595-7596. (i) Zhu, G.; Chen, Z.; Jiang, Q.; Xiao, D.; Cao, P.; Zhang, X. J. Am. Chem. Soc. 1997, 119, 3836-3837.
27. Xu, Z.; Lu, X. Tetrahedron Lett. 1997, 38, 3461-3464.
28. For preparative methods for N-tosylimines, see: (a) McKay, W. R.; Proctor, G. R. J. Chem. Soc., Perkin Trans. 1 1981, 2435-2442. (b) Love, B. E.; Raje, P. S.; Williams, T. C., II. Synlett 1994, 493-493. (c) Bilodeau, M. T.; Cunningham, A. M. J. Org. Chem. 1998, 63, 2800-2801. (d) Chemla, F.; Hebbe, V.; Normant, J.-F. Synthesis 2000, 75-77.
29. For preparative methods for N-tosylimines, see: (a) McKay, W. R.; Proctor, G. R. J. Chem. Soc., Perkin Trans. 1 1981, 2435-2442. (b) Love, B. E.; Raje, P. S.; Williams, T. C., II. Synlett 1994, 493-493. (c) Bilodeau, M. T.; Cunningham, A. M. J. Org. Chem. 1998, 63, 2800-2801. (d) Chemla, F.; Hebbe, V.; Normant, J.-F. Synthesis 2000, 75-77.
30. For preparative methods for N-tosylimines, see: (a) McKay, W. R.; Proctor, G. R. J. Chem. Soc., Perkin Trans. 1 1981, 2435-2442. (b) Love, B. E.; Raje, P. S.; Williams, T. C., II. Synlett 1994, 493-493. (c) Bilodeau, M. T.; Cunningham, A. M. J. Org. Chem. 1998, 63, 2800-2801. (d) Chemla, F.; Hebbe, V.; Normant, J.-F. Synthesis 2000, 75-77.
31. For preparative methods for N-tosylimines, see: (a) McKay, W. R.; Proctor, G. R. J. Chem. Soc., Perkin Trans. 1 1981, 2435-2442. (b) Love, B. E.; Raje, P. S.; Williams, T. C., II. Synlett 1994, 493-493. (c) Bilodeau, M. T.; Cunningham, A. M. J. Org. Chem. 1998, 63, 2800-2801. (d) Chemla, F.; Hebbe, V.; Normant, J.-F. Synthesis 2000, 75-77.
32. Preliminary experiments employing commercially available chiral phosphine (S,S)-DIPAMP to form 13e have indicated preferential formation of one enantiomer in moderate enantiomeric excess (34% ee), indicating involvement of the phosphine in a crucial carbon-carbon bond-forming step.
33. 11 See Supporting Information for a detailed experimental procedure.
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