Direct amino acid-catalyzed cascade reductive alkylation of arylacetonitriles: High-yielding synthesis of ibuprofen analogs

Tetrahedron Letters

Volumn 51, Issue 40, 2010, Pages 5246-5251

  Ramachary, Dhevalapally B ^a   Shiva Prasad, M ^a  

^a UNIVERSITY OF HYDERABAD   (India)

Author keywords

Amino acids; Cascade reactions; Ibuprofen analogs; Organocatalysis; TCRA reactions

Indexed keywords

(4 NITRO PHENYL)ACETONITRILE; 1,4 DIHYDROPYRIDINE; 2 ARYL 3 ALKYLPROPIONITRILE DERIVATIVE; 3,5 DIACETYL 1,4 DIHYDRO 2,6 DIMETHYLPYRIDINE; ACETONITRILE DERIVATIVE; ALDEHYDE DERIVATIVE; ARYLACETONITRILE DERIVATIVE; ARYLPROPIONIC ACID DERIVATIVE; BENZALDEHYDE; CARBON NITROGEN MONOCYCLE; IBUPROFEN DERIVATIVE; IMINIUM; KETONE DERIVATIVE; NONSTEROID ANTIINFLAMMATORY AGENT; PYRIDINE DERIVATIVE; SULFURIC ACID; UNCLASSIFIED DRUG;

AGRICULTURE; ALKYLATION; ARTICLE; CATALYSIS; CHEMICAL REACTION; DRUG INDUSTRY; ELECTRON; HYDROLYSIS;

EID: 77956340726     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2010.07.131     Document Type: Article

References (28)

1. M.R. Yadav, V.P. Pawar, S.M. Marvaniya, P.K. Halen, R. Giridhar, and A.K. Mishra Bioorg. Med. Chem. 16 2008 9443 9449
2. I. Andreu, I.M. Morera, F. Bosća, L. Sanchez, P. Camps, and M.A. Miranda Org. Biomol. Chem. 6 2008 860 867
3. J. Norinder, K. Bogar, L. Kanupp, and J.-E. Baeckvall Org. Lett. 9 2007 5095 5098
4. M.J. Bunegar, U.C. Dyer, G.R. Evans, R.P. Hewitt, S.W. Jones, N. Henderson, C.J. Richards, S. Sivaprasad, B.M. Skead, M.A. Stark, and E. Teale Org. Process Res. Dev. 3 1999 442 450
5. M. Jeanty, F. Suzenet, and G. Guillaumet J. Org. Chem. 73 2008 7390 7393
6. K. Motokura, N. Fujita, K. Mori, T. Mizugaki, K. Ebitani, K. Jitsukawa, and K. Kaneda Chem. Eur. J. 12 2006 8228 8239
7. P.J. Black, G. Cami-Kobeci, M.G. Edwards, P.A. Slatford, M.K. Whittlesey, and J.M.J. Williams Org. Biomol. Chem. 4 2006 116 125
8. P.A. Slatford, M.K. Whittlesey, and J.M.J. Williams Tetrahedron Lett. 47 2006 6787 6789
9. W. Chen, B. Liu, C. Yang, and Y. Xie Tetrahedron Lett. 47 2006 7191 7193
10. A. Loupy, M. Pellet, A. Petit, and G. Vo-Thanh Org. Biomol. Chem. 3 2005 1534 1540
11. K. Motokura, D. Nishimura, K. Mori, T. Mizugaki, K. Ebitani, and K. Kaneda J. Am. Chem. Soc. 126 2004 5662 5663
12. For recent papers on development of MCC reactions, see: D.B. Ramachary, K. Ramakumar, and V.V. Narayana J. Org. Chem. 72 2007 1458 1463
13. D.B. Ramachary, and R. Sakthidevi Org. Biomol. Chem. 6 2008 2488 2492
14. D.B. Ramachary, and Y.V. Reddy J. Org. Chem. 75 2010 74 85 and references cited therein
15. For recent papers on organocatalytic cascade and multi-component reactions, see: D.B. Ramachary, and C.F. Barbas III Chem. Eur. J. 10 2004 5323 5331
16. J.W. Yang, M.T. Hechavarria Fonseca, and B. List J. Am. Chem. Soc. 127 2005 15036 15037
17. Y. Huang, A.M. Walji, C.H. Larsen, and D.W.C. MacMillan J. Am. Chem. Soc. 127 2005 15051 15053
18. M. Marigo, S. Bertelsen, A. Landa, and K.A. Jorgensen J. Am. Chem. Soc. 128 2006 5475 5479
19. D. Enders, M.R.M. Huettl, C. Grondal, and G. Raabe Nature 441 2006 861 863
20. For recent papers on organocatalytic TCRA reactions for C-C/C-H bond formation, see: D.B. Ramachary, and M. Kishor J. Org. Chem. 72 2007 5056 5068
21. D.B. Ramachary, M. Kishor, and Y.V. Reddy Eur. J. Org. Chem. 2008 975 998
22. D.B. Ramachary, and M. Kishor Org. Biomol. Chem. 6 2008 4176 4187
23. We have not measured the enantiomeric purity of the hydrogenated products 6 (see Refs. 5a-c ).
24. For the discussion of selective formation of olefins via imine formation, see: T. Ishikawa, E. Uedo, S. Okada, and S. Saito Synlett 1999 450
25. R. Tanikaga, N. Konya, K. Hamamura, and A. Kaji Bull. Chem. Soc. Jpn. 61 1988 3211
26. For the determination of the electrophilicity parameters of olefins, see: O. Kaumanns, and H. Mayr J. Org. Chem. 73 2008 2738 2745
27. O. Kaumanns, R. Lucius, and H. Mayr Chem. Eur. J. 14 2008 9675 9682
28. CCDC-774736 for 5aa contains the supplementary crystallographic data for this paper. This data can be obtained free of charge via http://www.ccdc.cam.ac. uk/conts/retrieving.html or from the Cambridge Crystallographic Data Centre, 12, Union Road, Cambridge CB21EZ, UK; fax: +44 1223 336 033; or mailto:deposit@ccdc.cam.ac.uk.