Catalyst- and steric-controlled alkenylation via chemoselective C-H activation and C-Br activation in Heck reaction of methyl 1-(2-bromoaryl)-3-(2- furyl/thienyl)-5-oxopyrrolidine-2-carboxylates and diethyl 1-(2-bromoaryl)-3-(2- furyl/thienyl)-5-oxopyrrolidine-2,2-dicarboxylate derivatives

Tetrahedron Letters

Volumn 51, Issue 27, 2010, Pages 3580-3582

  Patra, Prasanta ^a   Ray, Jayanta K ^b   Kar, Gandhi K ^a  

^a PRESIDENCY UNIVERSITY   (India)

^b INDIAN INSTITUTE OF TECHNOLOGY   (India)

Author keywords

Lactam; C H activation; Chemoselective alkenylation; Electrophilic palladation; Heck reaction

Indexed keywords

CARBOXYLIC ACID DERIVATIVE; DIETHYL 1 (2 BROMOARYL) 3 (2 FURYL THIENYL) 5 OXOPYRROLIDINE 2 DICARBOXYLATE; ESTER DERIVATIVE; METHYL 1 (2 BROMOARYL) 3 (2 FURYL THIENYL) 5 OXOPYRROLIDINE 2CARBOXYLATE; UNCLASSIFIED DRUG;

ARTICLE; CATALYST; DRUG SYNTHESIS; HECK REACTION; OXIDATION; STEREOSPECIFICITY;

EID: 77954242797     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2010.05.005     Document Type: Article

References (18)

1. L.N. Jungheim, and R.J. Ternansky M.I. Page, The Chemistry of β-Lactams 1992 Blackie A & P. London 306 324
2. J.E. Baldwin, G.P. Lynch, and J. Pitlik J. Antibiot. 44 1991 1
3. J.E. Baldwin, C. Lowe, C.J. Schofield, and E. Lee Tetrahedron Lett. 27 1986 3461
4. D.B. Boyd, B.J. Foster, L.D. Hatfield, W.J. Hornback, N.D. Jones, J.E. Munroe, and J.K. Swartzendruber Tetrahedron Lett. 27 1986 3457
5. S. Harada, S. Tsubotani, T. Hida, K. Koyana, M. Kondo, and H. Ono Tetrahedron 44 1988 6589
6. G. Horvath, J. Gyimesi, and Z. Mehesfalvi-Vajna Tetrahedron Lett. 14 1973 3643
7. W. Fenical, P.R. Jensen, M.A. Palladino, K.S. Lam, G.K. Lloyd, and B.C. Potts Bioorg. Med. Chem. 17 2009 2175
8. R.R. Manam, V.R. Macherla, G. Tseung, C.W. Dring, J. Weiss, S.T.C. Neuteboom, K.S. Lam, and B.C. Potts J. Nat. Prod. 72 2009 295
9. J. Ondeyka, G. Harris, D. Zink, A. Basilio, F. Viciente, G. Bills, G. Platas, J. Collado, A. Gonzalez, M. de la Cruz, J. Martin, J.N. Kahn, S. Galuska, R. Giacobbe, G. Abruzzo, E. Hickey, P. Liberator, B. Jiang, D. Xu, T. Roemer, and S.B. Singh J. Nat. Prod. 72 2009 136
10. J.K. Ray, I. Sami, G.K. Kar, B.C. Roy, and N.K. Brahma Bioorg. Med. Chem. 2 1994 1417
11. G.K. Kar, B.C. Roy, S. Das adhikari, J.K. Ray, and N.K. Brahma Bioorg. Med. Chem. 6 1998 2397
12. R.F. Heck, and J.P. Nolley J. Org. Chem. 37 1972 2320
13. ++2+Na)]. (Supplementary physical and spectral data enclosed for other compounds.)
14. Y. Fujiwara, O. Maruyama, M. Yoshidomi, and H. Taniguchi J. Org. Chem. 46 1981 851
15. J. Tsuji, and H. Nagashima Tetrahedron 40 1984 2699
16. B.G. Chatterjee, and D.P. Sahu J. Org. Chem. 42 1977 3162
17. G.K. Kar, D. Ramesh, B.G. Chatterjee, and J.K. Ray J. Chem. Res. (M) 1997 568
18. G.K. Kar, D. Ramesh, B.G. Chatterjee, and J.K. Ray J. Chem. Res. (S) 1997 80