Highly enantioselective cycloisomerization of enynes catalyzed by rhodium for the preparation of functionalized lactams

Angewandte Chemie - International Edition

Volumn 41, Issue 23, 2002, Pages 4526-4529

  Lei, Aiwen ^a   Waldkirch, Jason P ^a   He, Minsheng ^a   Zhang, Xumu ^a  

^a PENNSYLVANIA STATE UNIVERSITY   (United States)

Author keywords

Enantioselectivity; Heterocycles; Homogeneous catalysis; Rhodium; Synthetic methods

Indexed keywords

CATALYSIS; RHODIUM; SUBSTRATES;

ENANTIOSELECTIVE FORMATION;

ISOMERIZATION;

2 PYRROLIDINONE; ALKYNE; BETA LACTAM ANTIBIOTIC; KETONE; LACTAM; MACROCYCLIC COMPOUND; RHODIUM;

ARTICLE; CATALYSIS; CHEMICAL REACTION; CHEMISTRY; CYCLIZATION; ENANTIOSELECTIVITY; ISOMERISM; STEREOISOMERISM; STRUCTURE ACTIVITY RELATION; SYNTHESIS;

ALKYNES; ANTI-BACTERIAL AGENTS; CATALYSIS; CYCLIZATION; LACTAMS; RHODIUM; STEREOISOMERISM; STRUCTURE-ACTIVITY RELATIONSHIP;

EID: 0037011395     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/1521-3773(20021202)41:23<4526::AID-ANIE4526>3.0.CO;2-K     Document Type: Article

References (48)

1. A. M. Rouhi, C&E News 2002, 80(23), 43-50.
2. a) S. Marukami, T. Takemoto, Z. Shimizu, J. Pharm. Soc. Jpn. 1953, 73, 1026-1028;
3. b) A. F. Parsons, Tetrahedron 1996, 52, 4149-4174.
4. a) K. Konno, H. Shirahama, T. Matsumoto, Tetrahedron Lett. 1983, 24, 939;
5. b) K. Konno, K. Hashimoto, Y. Ohfune, H. Shirahama, T. Matsumoto, J. Am. Chem. Soc. 1988, 110, 4807.
6. M. E. Garst, L. J. Dolby, S. Esfandiari, N. A. Fedoruk, N. C. Chamberlain, A. A. Avey, J. Org. Chem. 2000, 65, 7098, and references therein.
7. F. Khuong-Huu, X. Monseur, G. Ratle, G. Lukacs, R. Goutarel, Tetrahedron Lett. 1973, 14, 1757.
8. a) C. Aubert, O. Buisine, M. Malacria, Chem. Rev. 2002, 102, 813-834;
9. b) I. Ojima, M. Tzamarioudaki, Z. Li, R. J. Donovan, Chem. Rev. 1996, 96, 635-662;
10. c) B. M. Trost, Acc. Chem. Res. 1990, 23, 34;
11. d) B. M. Trost, M. J. Krische, Synlett 1998, 1;
12. e) B. M. Trost, Chem. Eur. J. 1998, 4, 2405.
13. a) B. M. Trost, M. Lautens, C. Chan, D. J. Jebaratnam, T. Mueller, J. Am. Chem. Soc. 1991, 113, 636-644, and references therein;
14. b) B. M. Trost, Y. Li, J. Am. Chem. Soc. 1996, 118, 6625-6633;
15. c) B. M. Trost, M. J. Krische, J. Am. Chem. Soc. 1999, 121, 6131-6141;
16. d) B. M. Trost, J. R. Corte, M. S. Gudiksen, Angew. Chem. 1999, 111, 3945-3947; Angew. Chem. Int. Ed. 1999, 38, 3662-3664;
17. d) B. M. Trost, J. R. Corte, M. S. Gudiksen, Angew. Chem. 1999, 111, 3945-3947; Angew. Chem. Int. Ed. 1999, 38, 3662-3664;
18. e) B. M. Trost, J. R. Corte Angew. Chem. 1999, 111, 3947-3949; Angew. Chem. Int. Ed. 1999, 38, 3664-3666;
19. e) B. M. Trost, J. R. Corte Angew. Chem. 1999, 111, 3947-3949; Angew. Chem. Int. Ed. 1999, 38, 3664-3666;
20. f) C. Fernandez-Rivas, M. Mendez, A. M. Echavarren, J. Am. Chem. Soc. 2000, 122, 1221-1222;
21. g) S. J. Sturla, N. M. Kablaoui, S. L. Buchwald, J. Am. Chem. Soc. 1999, 121, 1976-1977;
22. h) Y. Takayama, S. Okamoto, F. Sato, J. Am. Chem. Soc. 1999, 121, 3559-3560;
23. i) B. M. Trost, C. D. Haffner, D.J. Jebaratnam M. J. Krische, A. P. Thomas, J. Am. Chem. Soc. 1999, 121, 6183-6192.
24. a) M. Hatano, M. Terada, K. Mikami, Angew. Chem. 2001, 113, 255-259; Angew. Chem. Int. Ed. 2001, 40, 249-253;
25. a) M. Hatano, M. Terada, K. Mikami, Angew. Chem. 2001, 113, 255-259; Angew. Chem. Int. Ed. 2001, 40, 249-253;
26. b) A. Goeke, M. Sawamura, R. Kuwano, Y. Ito, Angew. Chem. 1996, 108, 686; Angew. Chem. Int. Ed. Engl. 1996, 35, 662.
27. b) A. Goeke, M. Sawamura, R. Kuwano, Y. Ito, Angew. Chem. 1996, 108, 686; Angew. Chem. Int. Ed. Engl. 1996, 35, 662.
28. B. M. Trost, C. Pedregal, J. Am. Chem. Soc. 1992, 114, 7292-7294.
29. X. Xie, X. Lu, Y. Liu, W. Xu, J. Org. Chem. 2001, 66, 6545-6550.
30. a) P. Cao, B. Wang, X. Zhang, J. Am. Chem. Soc. 2000, 122, 6490-6491;
31. b) P. Cao, X. Zhang, Angew. Chem. 2000, 112, 4270-4272; Angew. Chem. Int. Ed. 2000, 39, 4104-4106.
32. b) P. Cao, X. Zhang, Angew. Chem. 2000, 112, 4270-4272; Angew. Chem. Int. Ed. 2000, 39, 4104-4106.
33. Some other preliminary results for preparing lactones, and tetrahydrofurans will be published.
34. a) From the NMR spectra, there is clear evidence that all of these protected enyne amides are translcis-mixtures while the unprotected enyne amides are single isomers:
35. b) W. E. Stewart III, T. H. Siddall, Chem. Rev. 1970, 70, 517;
36. c) L. A. LaPlanche, M. T. Rogers, J. Am. Chem. Soc. 1963, 85, 3728.
37. The reactions of the substrates that contained E olefins were totally different. The reaction of -1c was examined; 20% conversion and 6% ee were obtained under the same conditions;
38. 1. F. R. Hartley, The Chemistry of Platinum and Palladium: With Particular Reference to Complexes of the Elements, Applied Science Publication Ltd, London, 1973, p. 377;
39. c) a terminal alkynyl-ene substrate was also examined in this reaction; high reactivity (100% conversion within 5 min) but poor enantioselectivity (6.5% ee) was observed.
40. a) M. Blouin, R. Frenette, J. Org. Chem. 2001, 66, 9043-9045. and references therein;
41. b) M. C. Croudace, N. E. Schore, J. Org. Chem. 1981, 46, 5357-5363.
42. L. Abraham, R. Czerwonka, M. Hiersemann, Angew. Chem. 2001, 113, 4835-4837; Angew. Chem. Int. Ed. 2001, 40, 4700-4703, and references therein.
43. L. Abraham, R. Czerwonka, M. Hiersemann, Angew. Chem. 2001, 113, 4835-4837; Angew. Chem. Int. Ed. 2001, 40, 4700-4703, and references therein.
44. B. M. Trost, J.-P. Surivet, Angew. Chem. 2001, 113, 1516-1519; Angew. Chem. Int. Ed. 2001, 40, 1468-1471, and references therein.
45. B. M. Trost, J.-P. Surivet, Angew. Chem. 2001, 113, 1516-1519; Angew. Chem. Int. Ed. 2001, 40, 1468-1471, and references therein.
46. Bn-substituted substrates failed to yield the desired 1,4-diene products, while the starting materials were completely consumed.
47. J. Tsuji, Transition Metal Reagents and Catalysts: Innovations in Organic Synthesis, Wiley, Chichester, 2000, pp. 10-14 and pp. 238-280.
48. Using freshly prepared 3a and freshly distilled solvent was important to achieve 99% ee.