Asymmetric organocatalytic Michael-type reaction of phosphorus ylides to nitroolefins: synthesis of γ-nitro-β-aryl-α-methylene carboxylic esters

Tetrahedron Letters

Volumn 51, Issue 2, 2010, Pages 446-448

  Allu, Suresh ^a   Selvakumar, Sermadurai ^a   Singh, Vinod K ^a,b  

^a INDIAN INSTITUTE OF TECHNOLOGY KANPUR   (India)

^b INDIAN INSTITUTE OF SCIENCE EDUCATION AND RESEARCH BHOPAL   (India)

Author keywords

[No Author keywords available]

Indexed keywords

ALKENE DERIVATIVE; ESTER DERIVATIVE; FORMALDEHYDE; GAMMA NITRO BETA ALPHA METHYLENE CARBOXYLIC ESTER; HYDROGEN; NITROOLEFIN; PHOSPHORUS; THIOUREA DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CATALYSIS; CHEMICAL BOND; CHEMICAL REACTION; CHEMICAL STRUCTURE; CONTROLLED STUDY; ENANTIOSELECTIVITY; HYDROGEN BOND; SYNTHESIS;

EID: 71049131612     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2009.11.063     Document Type: Article

References (43)

1. For selected examples on thiourea catalysis, see:. Sigman M.S., and Jacobsen E.N. J. Am. Chem. Soc. 120 (1998) 4901-4902
2. Okino T., Hoashi Y., and Takemoto Y. J. Am. Chem. Soc. 125 (2003) 12672-12673
3. Joly G.D., and Jacobsen E.N. J. Am. Chem. Soc. 126 (2004) 4102-4103
4. Yoon T.P., and Jacobsen E.N. J. Am. Chem. Soc. 44 (2005) 466-468
5. For a review on thiourea catalysis, see:. Connon S.J. Chem. Eur. J. 12 (2006) 5418-5427
6. Doyle A.G., and Jacobsen E.N. Chem. Rev. 107 (2007) 5713-5743
7. Takemoto Y. Org. Biomol. Chem. 3 (2005) 4299-4306
8. Schreiner P.R. Chem. Soc. Rev. 32 (2003) 289-296
9. For examples of Brønsted acid catalyzed enantioselective reactions, see:. McDougal N.T., and Schaus S.E. J. Am. Chem. Soc. 125 (2003) 12094-12095
10. Nugent B.M., Yoder R.A., and Johnston J.N. J. Am. Chem. Soc. 126 (2004) 3418-3419
11. For a review on Brønsted acid catalysis, see:. Jencks W.P. Acc. Chem. Res. 9 (1976) 425-432
12. Pihko P.M. Angew. Chem., Int. Ed. 43 (2004) 2062-2064
13. Bolm C., Rantanen T., Schiffers I., and Zani L. Angew. Chem., Int. Ed. 44 (2005) 1758-1763
14. Yamamoto H., and Fustatsugi K. Angew. Chem., Int. Ed. 44 (2005) 1924-1942
15. Akiyama T., Itoh J., and Fuchibe K. Adv. Synth. Catal. 348 (2006) 999-1010
16. Taylor M.S., and Jacobsen E.N. Angew. Chem., Int. Ed. 45 (2006) 1520-1543
17. Akiyama T. Chem. Rev. 107 (2007) 5744-5758
18. For a review, see:. Berner O.M., Tedeschi L., and Enders D. Eur. J. Org. Chem. (2002) 1877-1894
19. Maya V., and Singh V.K. Org. Lett. 9 (2007) 1117-1119
20. Asunskis J., and Shechter H. J. Org. Chem. 33 (1968) 1164-1168
21. von Strandtmann M., Cohen M.P., Puchalski C., and Shavel Jr. J. J. Org. Chem. 33 (1968) 4306-4309
22. Connor D.T., and von Strandtmann M. J. Org. Chem. 38 (1973) 1047-1049
23. For selected examples of stabilized sulfur ylides in organocatalytic reactions, see:. Aggarwal V.K., Alonso E., Hynd G., Lydon K.M., Palmer M.J., Porcelloni M., and Studley J.R. Angew. Chem., Int. Ed. 40 (2001) 1430-1433
24. Aggarwal V.K., Alonso E., Fang G., Ferrara M., Hynd G., and Porcelloni M. Angew. Chem., Int. Ed. 40 (2001) 1433-1436
25. Kunz R.K., and MacMillan D.W.C. J. Am. Chem. Soc. 127 (2005) 3240-3241
26. Zhang Y., Liu Y.-K., Kang T.-R., Hu Z.-K., and Chen Y.-C. J. Am. Chem. Soc. 130 (2008) 2456-2457
27. For selected examples see:. Okino T., Hoashi Y., Furukawa T., Xu X., and Takemoto Y. J. Am. Chem. Soc. 127 (2005) 119-125
28. Huang H., and Jacobsen E.N. J. Am. Chem. Soc. 128 (2006) 7170-7171
29. Tsogoeva S.B., and Wei S. Chem. Commun. (2006) 1451-1453
30. Wang J., Li H., Zu L., Jiang W., and Wang W. Adv. Synth. Catal. 348 (2006) 2047-2050
31. Wang J., Heikkinen L.D., Li H., Zu L., Jiang W., Xie H., and Wang W. Adv. Synth. Catal. 349 (2007) 1052-1056
32. Rabalakos C., and Wulff W.D. J. Am. Chem. Soc. 130 (2008) 13524-13525
33. Martin N.J.A., Cheng X., and List B. J. Am. Chem. Soc. 130 (2008) 13862-13863
34. Gao P., Wang C., Wu Y., Zhou Z., and Tang C. Eur. J. Org. Chem. (2008) 4563-4566
35. Dadwal M., Mohan R., Panda D., Mobin S.M., and Namboothri I.N.N. Chem. Commun. (2006) 338-340
36. Herrera R.P., Sgarzani V., Bernardi L., and Ricci A. Angew. Chem., Int. Ed 44 (2005) 6576-6579
37. Herrera R.P., Monge D., Martin-Zomora E., Fernández R., and Lassaletta J.M. Org. Lett. 9 (2007) 3303-3306
38. Martin N.J.A., Ozores L., and List B. J. Am. Chem. Soc. 129 (2007) 8976-8977
39. Rampalakos C., and Wulff W.D. Adv. Synth. Catal. 350 (2008) 1785-1790
40. Sohtome Y., Takemura N., Takagi R., Hashimoyo Y., and Nagasawa K. Tetrahedron 64 (2008) 9423-9429
41. Sibi M.P., and Itoh K. J. Am. Chem. Soc. 129 (2007) 8064-8065
42. Yar M., McGarrigle E.M., and Aggarwal V.K. Angew. Chem., Int. Ed. 47 (2008) 3784-3786
43. Zhu X.-F., Schaffner A.-P., Li R.C., and Kwon O. Org. Lett. 7 (2005) 2977-2980