Exploring the versatility of the Johnson-Claisen rearrangement: access to functionally versatile δ-ethoxycarbonyl-α,β-unsaturated nitriles

Tetrahedron

Volumn 66, Issue 16, 2010, Pages 3050-3057

  Cosgrove, Kelly L ^a   McGeary, Ross P ^a  

^a UNIVERSITY OF QUEENSLAND   (Australia)

Author keywords

Allylic alcohols; Cyanohydrins; Johnson Claisen rearrangement; Unsaturated nitriles

Indexed keywords

ALDEHYDE; ALPHA BETA ALDEHYDE; CYANOHYDRIN; GAMMA ETHOXYCARBONYL ALPHA BETA NITRILE; NITRILE; UNCLASSIFIED DRUG;

ARTICLE; CATALYSIS; CHEMICAL REACTION; HYDROLYSIS; JOHNSON CLAISEN REARRANGEMENT; PRIORITY JOURNAL;

EID: 77949568360     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2010.02.045     Document Type: Article

References (32)

1. Castro A.M.M. Chem. Rev. 104 (2004) 2939-3002
2. Johnson W.S., Werthemann L., Bartlett W.R., Brocksom T.J., Li T.-T., Faulkner D.J., and Peterson M.R. J. Am. Chem. Soc. 92 (1970) 741-743
3. Langlois Y. In: Hiersemann M., and Nubbemeyer U. (Eds). The Claisen Rearrangement-Methods and Applications (2007), Wiley-VCH, Weinheim 301-366
4. Giardina A., Marcantoni E., Mecozzi T., and Petrini M. Eur. J. Org. Chem. (2001) 713-718
5. Srikrishna A., and Nagaraju S. J. Chem. Soc., Perkin Trans. 1 (1992) 311-312
6. Cosgrove K.L., and McGeary R.P. Synlett (2009) 1749-1752
7. Burrows C.J., and Carpenter B.K. J. Am. Chem. Soc. 103 (1981) 6983-6984
8. Burrows C.J., and Carpenter B.K. J. Am. Chem. Soc. 103 (1981) 6984-6986
9. Aviyente V. J. Org. Chem. 62 (1997) 6121-6128
10. Yoo H.Y., and Houk K.N. J. Am. Chem. Soc. 119 (1997) 2877-2884
11. Gerrits P.J., Zumbragel F., and Marcus J. Tetrahedron 57 (2001) 8691-8698
12. Cosgrove K.L., and McGeary R.P. Synlett (2008) 2425-2428
13. Willams D.H., and Fleming I. Spectroscopic Methods in Organic Chemistry. 5th ed. (1995), McGraw-Hill, London, Sydney
14. Solis A., Luna H., Manjarrez N., and Perez H.I. Tetrahedron 60 (2004) 10427-10431
15. Jacobson R., Lahm G., and Clader J. J. Org. Chem. 45 (1980) 395-405
16. Kim S.S., and Lee S.H. Synth. Commun. 35 (2005) 751-759
17. Hayashi M., Miyamoto Y., Inoue T., and Oguni N. J. Org. Chem. 58 (1993) 1515-1522
18. Kiljunen E., and Kanerva L.T. Tetrahedron: Asymmetry 7 (1996) 1105-1116
19. Lu W., Chen P., and Lin G. Tetrahedron 64 (2008) 7822-7827
20. Brussee J., Loos W.T., Kruse C.G., and Van der Gen A. Tetrahedron 46 (1990) 979-986
21. Kirsten C.N., Herm M., and Schrader T.H. J. Org. Chem. 62 (1997) 6882-6887
22. Black P.J., Jenkins K., and Willams J.M.J. Tetrahedron: Asymmetry 13 (2002) 317-323
23. Ognyanov V.I., Datcheva V.K., and Kyler K.S. J. Am. Chem. Soc. 113 (1991) 6992-6996
24. Piancatelli G., and Leonelli F. Org. Synth. 83 (2006) 18-23
25. Anderson J.R., Edwards R.L., and Whalley A.J.S. J. Chem. Soc., Perkin Trans. 1 (1982) 215-221
26. Nanda S., Kato Y., and Asano Y. Tetrahedron: Asymmetry 17 (2006) 735-741
27. Kantam M.L., Mahendar K., Sreedhar B., Kumar K.V., and Choudary B.M. Synth. Commun. 38 (2008) 3919-3936
28. He B., Li Y., Feng X., and Zhang G. Synlett (2004) 1776-1778
29. Zgani I., Menut C., Seman M., Gallois V., Laffont V., Liautard J., Liautard J.-P., Criton M., and Montero J.-L. J. Med. Chem. 47 (2004) 4600-4612
30. Rajagopal G., Kim S.S., and George S.C. Appl. Organomet. Chem. 21 (2007) 198-202
31. Braish T.F., and Fuchs P.L. Synth. Commun. 15 (1985) 549-567
32. McGuirk P.R., and Collum D.B. J. Org. Chem. 49 (1984) 843-852