A novel approach to dihydropyrrolones from iron-substituted α,β-unsaturated imines and organolithium and grignard reagents: Developments, mechanisms and stereoselective syntheses

European Journal of Organic Chemistry

Volumn , Issue 24, 2000, Pages 3961-3969

  Rück Braun, Karola ^a   Amrhein, Patrick ^a  

^a JOHANNES GUTENBERG UNIVERSITY   (Germany)

Author keywords

Carbonylations; Grignard reactions; Iron; Lactams; Lithium; N sulfinylimines; Schiff bases

Indexed keywords

ALKADIENE; GAMMA LACTAM DERIVATIVE; IMINE; IRON DERIVATIVE; ORGANOLITHIUM COMPOUND; PYRROLE DERIVATIVE; REAGENT; SULFONYLDIHYDROPYRROLONE DERIVATIVE; UNCLASSIFIED DRUG;

CHEMICAL BINDING; CRYSTAL STRUCTURE; CYCLIZATION; REACTION ANALYSIS; SHORT SURVEY; STEREOCHEMISTRY; STRUCTURE ANALYSIS; SYNTHESIS;

EID: 0034519812     PISSN: 1434193X     EISSN: None     Source Type: Journal    
DOI: 10.1002/1099-0690(200012)2000:24<3961::aid-ejoc3961>3.0.co;2-p     Document Type: Review

References (68)

1. For recent developments/papers on syntheses of lactones and lactams catalyzed by transition metals, see: I. Collins, J. Chem. Soc., Perkin Trans. 1 1999, 1377-1395.
2. For recent developments, see: -
3. [2a] T. J. Donohoe, R. R. Harji, P. R. Moore, M. J. Warning, J. Chem. Soc., Perkin Trans. 1 1998, 819-834. -
4. [2b] A. C. Comely, S. E. Gibson (née Thomas), J. Chem. Soc., Perkin Trans. 1 1999, 223, and references cited.
5. S.-J. Shieh, K.-W. Liang, W.-T. Li, L.-H. Shu, M. Chandrasekharam, R.-S. Liu, Pure Appl. Chem. 1998, 70, 1111-1115.
6. S.-H. Wang, L.-H. Shiu, Y.-L. Liao, S.-L. Wang, G.-H. Lee, S.-M. Peng, R.-S. Liu, J. Am. Chem. Soc. 1996, 118, 530.
7. K.-W. Liang, W.-T. Li, S.-M. Peng, S. L. Wang, R. S. Liu, J. Am. Chem. Soc. 1997, 119, 4404-4412.
8. M. Chandrasekharam, S.-T. Chang, K.-W. Liang, W.-T. Li, R.-S. Liu, Tetrahedron Lett. 1998, 39, 643.
9. C.-C. Chen, J.-S. Fan, G.-H. Lee, S.-M. Peng, S.-L. Wang, R.-S. Liu, J. Am. Chem. Soc. 1996, 118, 9279-9287.
10. K. Rück-Braun, Angew. Chem. 1997, 109, 526-528;
11. Angew. Chem. Int. Ed. Engl. 1997, 36, 509-511.
12. K. Rück-Braun, T. Martin, M. Mikulás, Chem. Eur. J. 1999, 5, 1028-1037.
13. K. Rück-Braun, C. Möller, Chem. Eur. J. 1999, 5, 1038-1044.
14. C. Möller, M. Mikulás, F. Wierschem, K. Rück-Braun, Synlett 2000, 182-184.
15. M. Mikulás, S. Rust, D. Schollmeyer, K. Rück-Braun, Synlett 2000, 185-188.
16. H. Weingarten, J. P. Chupp, W. A. White, J. Org. Chem. 1967, 32, 3246-3249.
17. W. B. Jennings, C. J. Lovely, Tetrahedron Lett. 1988, 29, 3725-3728.
18. [15a] P. Amrhein, D. Schollmeyer, K. Rück-Braun, Organometallics, manuscript accepted for publication. -
19. [15b] P. Amrhein, D. Schollmeyer, K. Rück-Braun, manuscript submitted for publication.
20. [16a] G. Chelucci, A. Saba, Angew. Chem. 1995, 107, 104-106;
21. Angew. Chem. Int. Ed. Engl. 1995, 34, 78. -
22. [16b] C. Hulme, K. Moriarty, F.-C. Huang, J. Mason, D. McGarry, R. Labaudiniere, J. Souness, S. Djuric, Bioorg. Med. Chem. Lett. 1998, 8, 399-404. -
23. [16c] Z.-P. Zhuang, M.-P. Kung, M. Mu, H. F. Kung, J. Med. Chem. 1998, 41, 157-166.
24. L. S. Hegedus, Organische Synthese mit Übergangsmetallen, VCH, Weinheim, 1995, and references cited.
25. S. V. Ley, L. R. Cox, G. Meek, Chem. Rev. 1996, 96, 423, and references cited.
26. [19a] B. Denise, R. Goumont, A. Parlier, H. Rudler, J.-C. Daran, J. Vaissermann, J. Organomet. Chem. 1989, 377, 89-104. -
27. [19b] C. Bouancheau, M. Rudler, E. Chelain, H. Rudler, J. Vaissermann, J.-C. Daran, J. Organomet. Chem. 1995, 496, 125-135.
28. T. Morimoto, N. Chatani, S. Murai, J. Am. Chem. Soc. 1999, 121, 1758-1759, and references cited.
29. G. T. Crisp, A. G. Meyer, Tetrahedron 1995, 51, 5585-5596, and references cited.
30. S. M. Weinreb, Top. Curr. Chem. 1997, 190, 131-184.
31. [23a] J. Sisko, S. M. Weinreb, J. Org. Chem. 1990, 5, 393-395. -
32. [23b] M. T. Reetz, R. Jaeger, R. Drewlies, M. Hübel, Angew. Chem. 1991, 103, 76-78;
33. Angew. Chem. Int. Ed. Engl. 1991, 30, 101. -
34. [23c] M. Braun, K. Opdenbusch, Angew. Chem. 1993, 105, 595;
35. Angew. Chem. Int. Ed. Engl. 1993, 32, 578.
36. [24a] H. Nagashima, N. Ozaki, M. Washiyama, K. Itoh, Tetrahedron Lett. 1985, 26, 657-660. -
37. [24b] M. A. Casadei, A. Gessner, A. Inesi, W. Jugelt, F. M. Moracci, J. Chem. Soc., Perkin Trans. 1 1992, 2001-2004.
38. P. Amrhein, Diplomarbeit, Universität Mainz, 1997.
39. -3. Crystallographic data for 5a have been deposited with the Cambridge Crystallographic Data Base (deposition no. CCDC-137180). Copies of the data can be obtained free of charge on application to the CCDC, 12 Union Road, Cambridge CB2 1EZ, UK [Fax: (internat.) + 44-1223/336-033; E-mail: deposit@ccdc.cam.ac.uk].
40. -3. Crystallographic data for 5b have been deposited with the Cambridge Crystallographic Data Base (deposition no. CCDC-137181). Copies of the data can be obtained free of charge on application to the CCDC, 12 Union Road, Cambridge CB2 1EZ, UK [Fax: (internat.) + 44-1223/336-033; E-mail: deposit@ccdc.cam.ac.uk].
41. [28a] D Enders, U. Reinhold, Tetrahedron: Asymmetry 1997, 8, 1895-1946. -
42. [28b] H. Kunz, M. Weymann, M. Follmann, P. Allef, K. Oertel, M. Schultz-Kukula, A. Hofmeister, Pol. J. Chem. 1999, 73, 15-27. -
43. [28c] R. Bloch, Chem. Rev. 1998, 98, 1407-1438.
44. S. Itsuno, H. Yanaka, C. Hachisuka, K. Ito, J. Chem. Soc., Perkin Trans. 1 1991, 1341-1342.
45. [30a] F. A. Davis, P. Zhou, B.-C. Chen, Chem. Soc. Rev. 1998, 27, 13-18, and references cited. -
46. [30b] F. A. Davis, R. T. Reddy, W. Han, R. E. Reddy, Pure Appl. Chem. 1993, 65, 633-640. -
47. [30c] F. A. Davis, P. S. Portonovo, R. E. Reddy, G. V. Reddy, P. Zhou, Phosphorus Sulfur Silicon 1997, 120/121, 291-303, and references cited. -
48. [30d] R. Annunziata, M. Cinquini, F. Cozzi, J. Chem. Soc., Perkin Trans. 1 1982, 339-343.
49. [31a] F. A. Davis R E. Reddy, J. M. Szemwczyk, P. S. Protonova, Tetrahedron Lett. 1993, 34, 6229-6232. -
50. [31b] F. A. Davis, R. E. Reddy, J. M. Szemwczyk, G. V. Reddy, P. S. Portonovo, H. Zhang, D. Fanelli, R. T. Reddy, P. Zhou, P. J. Carroll, J. Org. Chem. 1997, 62, 2555-2563. -
51. [31c] F. A. Davis, Y. Zhang, Y. Andemichael, T. Fang, D. L. Fanelli, H. Zhang, J. Org. Chem. 1999, 64, 1403-1406. -
52. [31d] For the Peterson reaction, see: D. J. Ager, Synthesis 1984, 384-398.
53. D. H. Hua, S. W. Miao, J. S. Chen, S. Iguchi, J. Org. Chem. 1991, 56, 4-6.
54. T.-K. Yang, R.-Y. Chen, D.-S. Lee, W.-S. Peng, Y.-Z. Jiang, A.-Q. Mi, T.-T. Jong, J. Org. Chem. 1994, 59, 914.
55. P. Moreau, M. Essiz, J.-Y. Merour, D. Bouzard, Tetrahedron: Asymmetry 1997, 8, 591-598.
56. [35a] G. Liu, D. A. Cogan, J. A. Ellman, J. Am. Chem. Soc. 1997, 119, 9913-9914. -
57. [35b] G. Liu, D. A. Cogan, T. D. Owens, T. P. Tang, J. A. Ellman, J. Org. Chem. 1999, 64, 1278-1284.
58. [36a] D. A. Cogan, J. A. Ellman, J. Am. Chem. Soc. 1999, 121, 268-269. -
59. [36b] D. A. Cogan, G. Liu, J. Ellman, Tetrahedron 1999, 55, 8883-8904 and references cited therein.
60. K. Rück-Braun, P. Amrhein, unpublished results.
61. J. M. Klunder, K. B. Sharpless, J. Org. Chem. 1987, 52, 2598-2602.
62. -3. Crystallographic data for 28 have been deposited with the Cambridge Crystallographic Data Base (deposition no. CCDC-137182). Copies of the data can be obtained free of charge on application to the CCDC, 12 Union Road, Cambridge CB2 1EZ, UK [Fax: (internat.) + 44-1223/336-033; E-mail: deposit@ccdc.cam.ac.uk].
63. Y. Yamamoto, S. Nishii, K. Maruyama, T. Komatsu, W. Ito, J. Am. Chem. Soc. 1986, 108, 778-7786.
64. P. Bravo, M. Crucianelli, B. Vergani, M. Zanda, Tetrahedron Lett. 1998, 39, 7771-7774, and references cited.
65. J. L. Garcia-Ruano, R. Alonso, M. M. Zarzuelo, P. Noheda, Tetrahedron: Asymmetry 1995, 6, 1133-1142.
66. F. A. Davis, L. A. Jenkins, R. L. Billmers, J. Org. Chem. 1986, 51, 1033-1040.
67. F. A. Davis, R. E. Reddy, J. M. Szewczyk, J. Org. Chem. 1995, 60, 7037-7039.
68. F. A. Davis, R. L. Billmers, J. Am. Chem. Soc. 1981, 103, 7016-7018.