Iridium catalysed alkylation of tert-butyl cyanoacetate with alcohols under solvent free conditions

Tetrahedron

Volumn 65, Issue 4, 2009, Pages 849-854

  Grigg, Ronald ^a   Lofberg, Christian ^a   Whitney, Simon ^a   Sridharan, Visuvanathar ^a   Keep, Ann ^b   Derrick, Andrew ^c  

^a School of Chemistry University of Leeds Woodhouse Lane   (United Kingdom)

^b JOHNSON MATTHEY TECHNOLOGY CENTRE   (United Kingdom)

^c PFIZER GLOBAL RESEARCH AND DEVELOPMENT   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

ACETIC ACID DERIVATIVE; ALCOHOL DERIVATIVE; BENZYL ALCOHOL DERIVATIVE; IRIDIUM; SOLVENT;

ALKYLATION; ARTICLE; CATALYSIS; DECARBOXYLATION; DEGRADATION; HYDROLYSIS; PRIORITY JOURNAL; REACTION TIME; SUBSTITUTION REACTION;

EID: 57649106149     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2008.11.040     Document Type: Article

References (42)

1. Schreiber S.L. Science 287 (2000) 1964-1969
2. Spring D.R. Org. Biomol. Chem. 1 (2003) 3867-3870
3. Itami K., and Yoshida J.I. Chem.-Eur. J. 12 (2006) 3966-3974
4. Grigg R., Mitchell T.R.B., Sutthivaiyakit S., and Tongpenyai N. Tetrahedron Lett. 22 (1981) 4107-4711
5. Motokura K., Nishimura D., Mori K., Mizugaki T., Ebitani K., and Kaneda K. J. Am. Chem. Soc. 126 (2004) 5662-5663
6. Lofberg C., Grigg R., Whittaker M.A., Keep A., and Derrick A. J. Org. Chem. 71 (2006) 8023-8027
7. Lofberg C., Grigg R., Keep A., Derrick A., Sridharan V., and Kilner C. Chem. Commun. (2006) 5000-5002
8. Whitney S., Grigg R., Derrick A., and Keep A. Org. Lett. 9 (2007) 3299-3302
9. Cho C.S., Kim B.T., Kim T.J., and Shim S.C. J. Org. Chem. 6 (2001) 9020-9022
10. Cho C.S., Kim T.J., and Shim S.C. Tetrahedron Lett. 43 (2002) 7987-7990
11. Martinez R., Brand G.J., Ramon D.J., and Yus M. Tetrahedron Lett. 46 (2005) 3683-3686
12. Martinez R., Ramon D.J., and Yus M. Tetrahedron 62 (2006) 8982-8987
13. Martinez R., Ramon D.J., and Yus M. Tetrahedron 240 (2006) 8988-9001
14. Guillena G., Ramon D.J., and Yus M. Angew. Chem., Int. Ed. 46 (2007) 2-9
15. Yamada Y.M.A., and Uozumi Y. Org. Lett. 8 (2006) 1375-1378
16. Tauchi K., Nakagawa H., Hirabayashi T., Sakauchi S., and Ishii Y. J. Am. Chem. Soc. 126 (2004) 72-73
17. Edwards M.G., and Williams J.M.J. Angew. Chem., Int. Ed. 41 (2002) 4740-4743
18. Edwards M.G., Jazzar R.F.R., Paine B.M., Shermer D.J., Whittlesey M.K., Williams J.M.J., and Edney D.D. Chem. Commun. (2004) 90-91
19. Burling S., Pain B.M., Nama D., Brown V.S., Mahon M.F., Prior T.J., Pregosin P.S., Whittlesey M.K., and Williams J.M.J. J. Am. Chem. Soc. 129 (2007) 1987-1995
20. Slatford P.A., Whittlesey M.K., and Williams M.J. Tetrahedron Lett. 47 (2006) 6787-6789
21. Shibahara F., Bower J.F., and Krische M.J. J. Am. Chem. Soc. 130 (2008) 6338-6339
22. Bower J.F., Patman R.L., and Krische M.J. Org. Lett. 10 (2008) 1033-1035
23. Bower J.F., Skucas E., Patman R.L., and Krische M.J. J. Am. Chem. Soc. 129 (2007) 15134-15135
24. Ngai M.Y., Skucas E., and Krische M.J. Org. Lett. 10 (2008) 2705-2708
25. Patman R.L., Williams V.M., Bower J.F., and Krische M.J. Angew. Chem., Int. Ed. 47 (2008) 1-5
26. Grigg R., Mitchell T.R.B., Sutthivaiyakit S., and Tongpenyai N. J. Chem. Soc., Chem. Commun. (1981) 611-612
27. Watanabe Y., Tsuji Y., Ige H., Ohsugi Y., and Ohta T. J. Org. Chem. 49 (1984) 3359-3363
28. Fujita K., Fujii T., and Yamaguchi R. Org. Lett. 6 (2004) 3525-3528
29. Fujita K., and Yamaguchi R. Synlett (2005) 560-571
30. Fujita K., Asai C., Yamaguchi T., and Hanasaka F. Org. Lett. 7 (2005) 4017-4019
31. Fujita K., Enoki Y., and Yamaguchi R. Org. Synth. 83 (2006) 217-221
32. Haniti M., Hamid S.A., Slatford P.A., and Williams J.M. Adv. Synth. Catal. 349 (2007) 1555-1575
33. Hollmann D., Bahn S., Tillack A., and Beller M. Angew. Chem., Int. Ed. 46 (2007) 8291-8294
34. Hollmann D., Bahn S., Tillack A., and Beller M. Chem. Commun. (2008) 3199-3201
35. Cook J., Hamlin J.E., Nutton A., and Maitlis P.M. J. Chem. Soc., Dalton Trans. (1981) 2342-2352
36. Gill D.S., White C., and Maitlis P.M. J. Chem. Soc., Dalton Trans. (1978) 617-626
37. Maitlis P.M. Acc. Chem. Res. 11 (1978) 301-307
38. Spiteller P., and Von Nussbaum F. In: Juaristi E., and Soloshonok V.A. (Eds). Enantioselective Synthesis of β-Amino Acids. 2nd ed. (2005), Wiley-Interscience, Hoboken, NJ 19-93
39. Grigg R., Blacker J., Kilner C., McCaffrey S., Savic V., and Sridharan V. Tetrahedron 64 (2008) 8177-8181
40. Black P.J., Cami-Kobeci G., Edwards M.G., Slatford P.A., Whittlesey M.K., and Williams M.J. Org. Biomol. Chem. 4 (2006) 116-125
41. Morita M., Obora Y., and Ishii Y. Chem. Commun. (2007) 2850-2852
42. Ball R.G., Graham W.A.G., Heinekey D.M., Hoyano J.K., McMaster A.D., Mattson B.M., and Michel S.T. Inorg. Chem. 29 (1990) 2023-2025