Morita-Baylis-Hillman reaction of lactams and lactones with alkyl halides and epoxides catalyzed by hydroxysulfides

Organic Letters

Volumn 12, Issue 10, 2010, Pages 2418-2421

  Suarez Del Villar, Irene ^a   Gradillas, Ana ^a   Domínguez, Gema ^a   Pérez Castells, Javier ^a  

^a UNIVERSIDAD SAN PABLO CEU   (Spain)

Author keywords

[No Author keywords available]

Indexed keywords

EPOXIDE; HALOGENATED HYDROCARBON; LACTAM; LACTONE; SULFIDE;

ARTICLE; CATALYSIS; CHEMICAL STRUCTURE; CHEMISTRY; STEREOISOMERISM;

CATALYSIS; EPOXY COMPOUNDS; HYDROCARBONS, HALOGENATED; LACTAMS; LACTONES; MOLECULAR STRUCTURE; STEREOISOMERISM; SULFIDES;

EID: 77952412961     PISSN: 15237060     EISSN: 15237052     Source Type: Journal    
DOI: 10.1021/ol100788g     Document Type: Article

References (36)

1. Reviews
2. Basavaiah, D.; Rao, A. J.; Satyanarayana, T. Chem. Rev. 2003, 103, 811-891
3. Singh, V.; Batra, S. Tetrahedron 2008, 64, 4511-4574
4. Basavaiah, D.; Rao, K.; Venkateswara, R.; Raju, J. Chem. Soc. Rev. 2007, 36, 1581-1588
5. Basavaiah, D.; Rao, P. D.; Hyma, R. S. Tetrahedron 1996, 52, 8001-8062
6. Reviews on aza-MBH
7. Declerck, V.; Martinez, J.; Lamaty, F. Chem. Rev. 2009, 109, 1-48
8. Shi, Y. S.; Shi, M. Eur. J. Org. Chem. 2007, 2905-2916
9. For recent appications of phosphine-catalyzed MBH-type reactions, see
10. Webber, P.; Krische, M. J. J. Org. Chem. 2008, 73, 9379-9387
11. Koech, P. K.; Krische, M. J. Tetrahedron 2006, 62, 10594-10602
12. Koech, P. K.; Krische, M. J. J. Am. Chem. Soc. 2004, 126, 5350-5351
13. Jellerich, B. G.; Kong, J.-R.; Krische, M. J. J. Am. Chem. Soc. 2003, 125, 7758-7759
14. Krishna, P. R.; Sachwani, R.; Reddy, P. Synlett 2008, 289, 7-2912
15. Masson, G.; Housseman, C.; Zhu, J. Angew. Chem., Int. Ed. 2007, 46, 4614-4628
16. Kataoka, T.; Iwama, T.; Tsujiyama, S.-I. Chem. Commun. 1998, 197-198
17. Kataoka, T.; Iwama, T.; Tsujiyama, S.-I.; Iwamura, T.; Watanabe, S.-I. Tetrahedron 1998, 54, 11813-11824
18. Langer, P. Angew. Chem., Int. Ed. 2000, 39, 3049-3052
19. Kataoka, T.; Kinoshita, H.; Iwama, T.; Tsujiyama, S.-I.; Iwamura, T.; Watanabe, S.-I.; Muraokab, O.; Tanabe, G. Tetrahedron 2000, 56, 4725-4731
20. Iwama, T.; Tsujiyama, S.; Kinoshita, H.; Kanematsu, K.; Tsurukami, Y.; Iwamura, T.; Watanabe, S.-I.; Kataoka, T. Chem. Pharm. Bull. 1999, 47, 956-961
21. Kataoka, T.; Iwama, T.; Tsujiyama, S.; Kanematsu, K.; Iwamura, T.; Watanabe, S.-I. Chem. Lett. 1999, 257-258
22. Aroyan, C. E.; Miller, S. J. J. Am. Chem. Soc. 2007, 129, 256-257
23. Wang, L.-C.; Luis, A. L.; Agapiou, K.; Jang, H.-Y.; Krische, M. J. J. Am. Chem. Soc. 2002, 124, 2402-2403
24. Basavaiah, D.; Sharada, D. S.; Kumaragurubaran, N.; Reddy, R. M. J. Org. Chem. 2002, 67, 7135-7137
25. Basavaiah, D.; Kumaragurubaran, N.; Sharada, D. S. Tetrahedron Lett. 2001, 42, 85-87
26. Krafft, M. E.; Haxell, T. F. N. J. Am. Chem. Soc. 2005, 127, 10168-10169
27. Krafft, M. E.; Seibert, K. A. Synlett 2006, 3334-3336
28. Krafft, M. E.; Seibert, K. A.; Haxell, T. F. N.; Hirosawa, C. Chem. Commun. 2005, 5772-5774
29. Krafft, M. E.; Haxell, T. F. N.; Seibert, K. A.; Abboud, K. A. J. Am. Chem. Soc. 2006, 128, 4174-4175
30. Hill, J. S.; Isaacs, N. S. J. Phys. Org. Chem. 1990, 285-293
31. Basavaiah, D.; Sarma, P. K. Synth. Commun. 1990, 20, 1611-1615
32. Ye, S.; Huang, Z. Z.; Xia, C.-A.; Tang, Y.; Dai, L.-X. J. Am. Chem. Soc. 2002, 124, 2432-2433
33. 3S (367.46): C, 68.64; H, 5.76; N, 3.81. Found: C, 68.56; H, 5.57; N, 3.65.
34. The only precedent in the use of epoxides in MBH reactions is an intramolecular phosphine-catalyzed reaction
35. Krafft, M. E.; Wright, J. A. Chem. Commun. 2006, 2977-2979
36. The ee was 3%, determined by HPLC using a CHIRAL-AGP column (100 × 4.0 mm); with 9% 2-propanol in 10 mM sodium phosphate buffer as mobile phase; pH = 7.0; flow rate = 0.9 mL/min.