Diastereoselective synthesis of γ-lactams by a one-pot, four-component reaction

Organic Letters

Volumn 9, Issue 20, 2007, Pages 4077-4080

  Jingqiang, Wei ^a   Shaw, Jared T ^a,b  

^a MASSACHUSETTS INSTITUTE OF TECHNOLOGY   (United States)

^b UNIVERSITY OF CALIFORNIA   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ACID ANHYDRIDE; IMIDE; LACTAM;

ARTICLE; CHEMICAL STRUCTURE; CHEMISTRY; STEREOISOMERISM; SYNTHESIS;

ANHYDRIDES; IMIDES; LACTAMS; MODELS, MOLECULAR; MOLECULAR STRUCTURE; STEREOISOMERISM;

EID: 35048870516     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol701911u     Document Type: Article

References (37)

1. (a) Bienayme, H.; Hulme, C.; Oddon, G.; Schmitt, P. Chem.-Eur. J. 2000, 6, 3321-3329.
2. (b) Zhu, J., Bienayme, H., Eds. Multicomponent Reactions; Wiley-VCH: Weinheim, Germany, 2005; p 468.
3. (a) Hantzsch, A. Liebigs Ann. Chem. 1882, 215, 1-82.
4. (b) Simon, C.; Constantieux, T.; Rodriguez, J. Eur. J. Org. Chem. 2004, 4957-4980.
5. (a) Biginelli, P. Ber. Dtsch. Chem. Ges. 1891, 24, 2962-2967.
6. (b) Kappe, C. O.; Stadler, A. Org. React. (NY) 2004, 63, 1-116.
7. (a) Passerini, M. Gazz. Chim. Ital. 1921, 51, 181-189.
8. (b) Banfi, L.; Riva, R. Org. React. (NY) 2005, 65, 1-140.
9. (a) Ugi, I.; Meyr, R.; Fetzer, U.; Steinbruckner, C. Angew. Chem. 1959, 71, 386.
10. (b) Dömling, A.; Ugi, I. Angew. Chem., Int. Ed. 2000, 39, 3168-3210.
11. (c) Dömling, A. Chem. Rev. 2006, 106, 17-89.
12. (a) Petasis, N. A.; Akritopoulou, I. Tetrahedron Lett. 1993, 34, 583-586.
13. (b) Petasis, N. A.; Zavialov, I. A. J. Am. Chem. Soc. 1997, 119, 445-446.
14. (a) For an example of a five-component reaction in which hexasubstituted benzenes are produced in a one-pot sequential process, see: Janvier, P.; Bienayme, H.; Zhu, J. Angew. Chem., Int. Ed. 2002, 41, 4291-4294.
15. (b) For an example of a seven-component reaction, see: Dömling, A.; Ugi, I. Angew. Chem., Int. Ed. 1993, 32, 563-564.
16. For direct comparison, we are limiting our description of 3CRs and 4CRs to those in which all of the components can be independently varied. The Hantzsch, Biginelli, Passerini, and Petasis 3CRs and the Ugi 4CR are all examples of MCRs in which each component can, to a certain extent, be varied independently. For a comprehensive discussion of many MCRs discovered to date, see ref 1.
17. Ng, P. Y.; Masse, C. E.; Shaw, J. T. Org. Lett. 2006, 8, 3999-4002.
18. Stephani, R.; Cesare, V.; Sadarangani, I.; Lengyel, I. Synthesis 2002, 47-52.
19. (a) Rosenfield, R. E., Jr.; Dunitz, J. D. Helv. Chim. Acta 1978, 61, 2176-2189.
20. (b) Kayser, M. M.; Wipff, G. Can. J. Chem. 1982, 60, 1192-1198.
21. See Supporting Information. A related 3CR with homophthalic anhydride has been observed: Yadav, J. S.; Reddy, B. V. S.; Saritha Raj, K.; Prasad, A. R. Tetrahedron 2003, 59, 1805-1809.
22. The S-aryl compounds are useful substrates for radical reactions. See: (a) Ikeda, M.; Hamada, M.; Yamashita, T.; Matsui, K.; Sato, T.; Ishibashi, H. J. Chem. Soc., Perkin Trans. 1999, 1, 1949-1956.
23. (b) Alibes, R.; Bayon, P.; De March, P.; Figueredo, M.; Font, J.; Marjanet, G. Org. Lett. 2006, 8, 1617-1620.
24. (c) Ghosh, S.; Sinha, S.; Drew, M. G. B. Org. Lett. 2006, 8, 3781-3784.
25. Alkyl-substituted maleic anhydrides are easily prepared from Grignard reagents and dimethylacetylene dicarboxylate: (a) Scholte, A. A.; Eubanks, L. M.; Poulter, C. D.; Vederas, J. C. Bioorg. Med. Chem. 2004, 12, 163-110.
26. See refs 16a and 16b. The reaction of the thiol with the anhydride in the presence of base is rapid at room temperature: Zienty, F. B.; Vineyard, B. D.; Schleppnik, A. A. J. Org. Chem. 1962, 27, 3140-3146. When the thiol, amine, and anhydride are combined at rt, some of the thio-substituted anhydride could form since the addition of the amine to the anhydride is probably competitive with the base-mediated conjugate addition of the thiol. Compounds 31-33 are all observed in the crude reaction mixture before the reaction mixture is heated to induce the condensation with the aldehyde.
27. The conjugate addition of thiols to maleic monoamides has been reported to occur at the β-carbon of the amide: (a) Augustin, M.; Mueller, W. Z. Chem. 1985, 25, 61-62.
28. (b) Neumann, R.; Ringsdorf, H. J. Am. Chem. Soc. 1986, 108, 487-490. The presence of the other regioisomers is not ruled out in either report. For related studies on thiol conjugate addition to mixed amide/ester and ester/acid maleates, see:
29. (c) Augustin, M.; Koehler, M. Tetrahedron 1976, 32, 2141-2145.
30. (d) Tomioka, K.; Muraoka, A.; Kanai, M. J. Org. Chem. 1995, 60, 6188-6190.
31. (e) Kamimura, A.; Murakami, N.; Kawahara, F.; Yokota, K.; Omata, Y.; Matsuura, K.; Oishi, Y.; Morita, R.; Mitsudera, H.; Suzukawa, H.; Kakehi, A.; Shirai, M.; Okamoto, H. Tetrahedron 2003, 59, 9537-9546.
32. (f) Kamimura, A.; Murakami, N.; Yokota, K.; Shirai, M.; Okamoto, H. Tetrahedron Lett. 2002, 43, 7521-7523.
33. (g) Schmidt, T. J.; Ak, M.; Mrowietz, U. Bioorg. Med. Chem. 2007, 15, 333-342.
34. (a) Mehta, N. B.; Phillips, A. P.; Lui, F. F.; Brooks, R. E. J. Org. Chem. 1960, 25, 1012-1015.
35. (b) Baydar, A. E.; Boyd, G. V.; Aupers, J.; Lindley, P. F. J. Chem. Soc., Perkin Trans. 1981, 1, 2890-2894. Mehta et al. report that primary amines react unselectively with 3-methylmaleic (citraconic) anhydride, whereas secondary amines were reported to react with >95% regioselectivity. The subsequent report from Baydar demonstrates that these findings were incorrect and that both primary and secondary amines exhibit 50:50 to 78:22 regioselectivity.
36. (a) Natsugari, H.; Matsushita, Y.; Tamura, N.; Yoshioka, K.; Ochiai, M. J. Chem. Soc., Perkin Trans. 1983, 1, 403-411.
37. (b) Kametani, T.; Kawamura, K.; Honda, T. J. Am. Chem. Soc. 1987, 109, 3010-3017.