New approaches to polysubstituted pyrroles and y-lactams based on nucleophilic addition of Ti(IV) enolates derived from α-diazo-β-keto carbonyl compounds to N-tosylimines

Journal of Organic Chemistry

Volumn 71, Issue 15, 2006, Pages 5560-5564

  Dong, Changqing ^a   Deng, Guisheng ^a   Wang, Jianbo ^a  

^a PEKING UNIVERSITY   (China)

Author keywords

[No Author keywords available]

Indexed keywords

ADDITION REACTIONS; CATALYSIS; DECOMPOSITION; ESTERS; KETONES; SUBSTITUTION REACTIONS;

DIAZO DECOMPOSITION; N-TOSYLIMINES; PHOTOINDUCED CONDITIONS; POLYSUBSTITUTED PYRROLES;

POLYPYRROLES;

ALPHA DIAZO BETA KETO CARBONYL DERIVATIVE; CARBONYL DERIVATIVE; CHLORIDE; ESTER; GAMMA LACTAM DERIVATIVE; IMINE; KETONE; N TOSYLIMINE; PYRROLE; PYRROLE DERIVATIVE; RHODIUM; TITANIUM; UNCLASSIFIED DRUG;

ADDITION REACTION; ALDOL REACTION; ANNULATION REACTION; ARTICLE; CATALYSIS; DECOMPOSITION; DIASTEREOISOMER; IRRADIATION; MANNICH REACTION; MUKAIYAMA REACTION; PHOTOLYSIS; POLYMERIZATION; REACTION ANALYSIS; STEREOCHEMISTRY; WOLFF REARRANGEMENT;

EID: 33746329351     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo0605039     Document Type: Article

References (59)

1. For recent reviews on the chemistry of pyrroles, see: (a) Comprehensive Heterocyclic Chemistry; Bird, C. W., Ed.; Pergamon Press: Oxford, UK, 1996; Vol. 2.
2. (b) Joule, J. A.; Mills, K. In Heterocyclic Chemistry; Blackwell Science: Oxford, UK, 2000; Chapter 13.
3. (c) Balme, G. Angew. Chem., Int. Ed. 2004, 43, 6238.
4. For a review of pyrrole structure in materials, see: Electronic Materials: The Oligomer Approach; Müllen, K., Wegner, G., Eds.; Wiley-VCH: Weinheim, Germany, 1998.
5. Li, J. J. Name Reactions: A Collection of Detailed Reaction Mechanisms; Springer-Verlag: Berlin, Germany, 2002.
6. For recent examples of Hantzsch synthesis of pyrroles, see: (a) Kameswaran, V.; Jiang, B. Synthesis 1997, 5, 530-532.
7. (b) Trautwein, A. W.; Sussmuth, R. D.; Jung, G. Bioorg. Med. Chem. Lett. 1998, 8, 2381-2384.
8. (c) Palacios, F.; Aparicio, D.; de los Santos, J. M.; Vicario, J. Tetrahedron 2001, 57, 1961-1972.
9. (d) Matiychuk, V. S.; Martyak, R. L.; Obushak, N. D.; Ostapiuk, Yu. V.; Pidlypnyi, N. I. Chem. Heterocycl. Compd. (N.Y., NY, U.S.) 2004, 40, 1218-1219.
10. For recent examples of Paal-Knorr reaction, see: (a) Minetto, G.; Raveglia, L. F.; Sega, A.; Taddei, M. Eur. J. Org. Chem. 2005, 5277-5288.
11. (b) Banik, B. K.; Banik, I.; Renteria, M.; Dasgupta, S. K. Tetrahedron Lett. 2005, 46, 2643-2645.
12. (c) Bharadwaj, A. R.; Scheldt, K. A. Org. Lett. 2004, 6, 2465-2468.
13. (d) Minetto, G.; Raveglia, L. F.; Taddei, M. Org. Lett. 2004, 6, 389-392.
14. (e) Banik, B. K.; Samajdar, S.; Banik, I. J. Org. Chem. 2004, 69, 213-216.
15. (f) Wang, B.; Gu, Y.; Luo, C.; Yang, T.; Yang, L.; Suo, J. Tetrahedron Lett. 2004, 45, 3417-3419.
16. For an example of Knorr pyrrole synthesis, see: Alberola, A.; Onega, A. G.; Sadaba, M. L.; Sanudo, C. Tetrahedron 1999, 55, 6555-6566.
17. For recent examples on the pyrrole synthesis based on the transition metal catalyzed process, see: (a) Takaya, H.; Kojima, S.; Murahashi, S.-I. Org. Lett. 2001, 3, 421-424.
18. (b) Kel'in, A. V.; Sromek, A. W.; Gevorgyan, V. J. Am. Chem. Soc. 2001, 123, 2074-2075.
19. (c) Gabriele, B.: Salerno, G.; Fazio, A. J. Org. Chem. 2003, 68, 7853-7861.
20. (d) Ramanathan, B.; Keith, A. J.; Armstrong, D.; Odom, A. L. Org. Lett. 2004, 6, 2957-2960.
21. (e) Shen, H.-C.; Li, C.-W.; Liu, R.-S. Tetrahedron Lett. 2004, 45, 9245-9247.
22. (f) Wurz, R. P.; Charette, A. B. Org. Lett. 2005, 7, 2313-2316.
23. (g) Kamijo, S.; Kanazawa, C.; Yamamoto, Y. J. Am. Chem. Soc. 2005, 127, 9260-9266.
24. (h) Gorin, D. J.; Davis, N. R.; Toste, F. D. J. Am. Chem. Soc. 2005, 127, 11260-11261.
25. (i) Larionov, O. V.; de Meijere, A. Angew. Chem., Int. Ed. 2005, 44, 5664-5667.
26. For recent reviews on y-lactam synthesis, see: (a) Huang, P.-Q. In New Methods for the Asymmetric Synthesis of Nitrogen Heterocycles; Research Signpost: Trivandrum, India, 2005, pp 197-222.
27. (b) Smith, M. B. In Science of Synthesis; Weinreb, S., Ed; Georg Thieme Verlag: Stuttgart, Germany, 2005; Vol. 21, pp 647-711.
28. Recent examples of the synthesis of γ-lactams by ring expansions, see: (a) Banfi, L.; Guanti, G.; Rasparini, M. Eur. J. Org. Chem. 2003, 1319-1336.
29. (b) Alcaide, B.; Almendros, P.; Alonso, J. M. J. Org. Chem. 2004, 69, 993-996.
30. (c) Park, J.-H.; Ha, J.-R.; Oh, S.-J.; Kim, J.-A.; Shin, D.-S.; Won, T.-J.; Lam, Y.-F.; Ahn, C. Tetrahedron Lett. 2005, 46, 1755-1757.
31. (d) Alcaide, B.; Almendros, P.; Cabrero, G.; Ruiz, M. P. Org. Lett. 2005, 7, 3981-3984.
32. For examples of [3+2] annulations in γ-lactam synthesis, see: (a) Roberson, C. W.; Woerpel, K. A. J. Org. Chem. 1999, 64, 1434-1435.
33. (b) Sun, P.-P.; Chang, M.-Y.; Chiang, M. Y.; Chang, N.-C. Org. Lett. 2003, 5, 1761-1763.
34. For the recent examples of γ-lactam synthesis by metal carbene intramolecular C-H insertions, see: (a) Yoon, C. H.; Zaworotko, M. J.; Moulton, B.; Jung, K. W. Org. Lett. 2001, 3, 3539-3542.
35. (b) Wee, A. G. H.; Duncan, S. C. Tetrahedron Lett. 2002, 43, 6173-6179.
36. (c) Yoon, C. H.; Nagle, A.; Chen, C.; Gandhi, D.; Jung, K. W. Org. Lett. 2003, 5, 2259-2262.
37. (d) Choi, M. K.-W.; Yu, W.-Y.; Che, C.-M. Org. Lett. 2005, 7, 1081-1084.
38. (e) Wee, A. G. H.; Duncan, S. C.; Fan, G.-j. Tetrahedron: Asymmetry 2006, 17, 297-307.
39. For comprehensive reviews on the chemistry of a-diazocarbonyl compounds, see: (a) Ye, T.; McKervey, M. A. Chem. Rev. 1994, 94, 1091-1160.
40. (b) Doyle, M. P.; McKervey, M. A.; Ye, T. In Modern Catalytic Methods for Organic Synthesis with Diazo Compounds', Wiley-Interscience: New York, 1998.
41. For an account, see: Zhao, Y.; Wang, J. Synlett 2005, 2886-2892.
42. Part of this investigation has been reported in a communication, see: Deng, G.; Jiang, N.; Ma, Z.; Wang, J. Synlett 2002, 1913-1915.
43. For intramolecular N-H bond insertion in the synthesis of 3-pyrrolidinone derivatives, see: (a) Moyer, M. P.; Feldman, P. L.; Rapoport, H. J. Org. Chem. 1985, 50, 5223-5230.
44. (b) Wang, J.; Hou, Y.; Wu, P. J. Chem. Soc., Perkin Trans. 1 1999, 2277-2280.
45. (c) Davis, F. A.; Fang, T.; Goswami, R. Org. Lett. 2002, 4, 1599-1602.
46. (a) Wang, J.; Hou, Y. J. Chem. Soc., Parkin Trans. 1 1998, 1919-1924.
47. (b) Wang, J.; Hou, Y.; Wu, P.; Qu, Z.; Chan, A. S. C. Tetrahedron: Asymmetry 1999, 10, 4553-4561.
48. (c) Lee, D. J.; Kim, K.; Park, Y. J. Org. Lett. 2002, 4, 873-876.
49. (d) For a recent review on Wolff rearrangement, see:
50. (e) Kirmse, W. Eur. J. Org. Chem. 2002, 2193-2256.
51. (a) Calter, M. A.; Sugathapala, P. M.; Zhu, C. Tetrahedron Lett. 1997, 38, 3837-3840.
52. (b) Calter, M. A.; Sugathapala, P. M. Tetrahedron Lett. 1998, 39, 8813-8816.
53. (c) Calter, M. A.; Zhu, C. J. Org. Chem. 1999, 64, 1415-1419.
54. We have extended the reaction of Ti(IV) enolate 8 with ketones, see: Deng, G.; Tian, X.; Wang, J. Tetrahedron Lett. 2003, 44, 587-590.
55. Doyle, M. P.; Kundu, K.; Russell, A. E. Org. Lett. 2005, 7, 3131-3134.
56. Itoh, Y.; Yamanaka, M.; Mikami, K. J. Am. Chem. Soc. 2004, 126, 13174-13175.
57. For a mechanistic investigation on Rh(II) complex mediated diazo decomposition, see: Qu, Z.; Shi, W.; Wang, J. J. Org. Chem. 2001, 66, 8139-8144 and references therein.
58. (a) Noguchi, Y.; Kurogi, K.; Sekioka, M.; Furukawa, M. Bull. Chem. Soc. Jpn. 1983, 56, 349-350.
59. (b) Sas, W. J. Chem. Res. Synop. 1993, 160-161.