A study on the regioselectivity in N,C-acylation of β-enamino-esters

Tetrahedron

Volumn 69, Issue 23, 2013, Pages 4586-4590

  Defant, Andrea ^a   Mancini, Ines ^a  

^a UNIVERSITY OF TRENTO   (Italy)

Author keywords

Enamino ester; Amino pyrone; N,C Acylation; Regioselectivity

Indexed keywords

4 (BENZYLAMINO) 6 METHYL 2H PYRAN 2 ONE; ACID HALIDE; AMIDE; AMINE; BETA ENAMINO ESTER; DICHLOROMETHANE; ESTER DERIVATIVE; PYRONE DERIVATIVE; TRIETHYLAMINE; UNCLASSIFIED DRUG;

ACYLATION; ARTICLE; CHEMICAL REACTION; CHEMICAL STRUCTURE; HYDROGEN BOND; PRIORITY JOURNAL; REGIOSELECTIVITY; SOLVENT EFFECT;

EID: 84877005548     PISSN: 00404020     EISSN: 14645416     Source Type: Journal    
DOI: 10.1016/j.tet.2013.04.012     Document Type: Article

References (16)

1. J. Wang, J.J. Swidorski, N. Sydorenko, R.P. Hsung, H.A. Coverdale, J.M. Kuyava, and J. Liu Heterocycles 70 2006 423 459
2. H.M. Sklenicka, R.P. Hsung, M.J. McLaughlin, L. Wei, A.I. Gerasyuto, and W.B. Brennessel J. Am. Chem. Soc. 124 2002 10435 10442
3. M.J. McLaughlin, R.P. Hsung, K.P. Cole, J.M. Hahn, and J. Wang J. Org. Lett. 4 2002 2017 2020
4. R.P. Hsung, L. Wei, H.M. Sklenicka, C.J. Douglas, M.J. McLaughlin, J.A. Mulder, and L. Yao J. Org. Lett. 1 1999 509 512
5. G. Negri, C. Kascheres, and A.J. Kascheres J. Heterocycl. Chem. 41 2004 461 491
6. H. Menghezzi, A. Boucekkine, B. Kolli, and M. Hamdi Int. J. Quantum Chem. XXIV 1983 425 428
7. Preliminary results were presented at the 16th Electronic Conference on Synthetic Organic Chemistry (ECSOC), November 2012.
8. C.A.G.N. Montalbetti, and V. Falque Tetrahedron 61 2005 10827 10852
9. B.G. Hazara, V.S. Pore, and S.P. Maybhate Org. Prep. Proc. Int. 21 1989 355 358
10. H. Mayr, M. Breugst, and A.R. Ofial Angew. Chem., Int. Ed. 50 2011 6470 6505
11. J.A. King Jr., and G.L. Bryant Jr. J. Org. Chem. 57 1992 5136 5139
12. P. Jaramillo, P. Pérez, and P. Fuentealba J. Phys. Org. Chem. 20 2007 1050 1057
13. M.N. Eberlin, Y. Takahata, and C. Kascheres J. Org. Chem. 55 1990 5150 5155
14. M.J. Frisch, G.W. Trucks, H.B. Schlegel, G.E. Scuseria, M.A. Robb, J.R. Cheeseman, J.A. Montgomery, T. Vreven Jr., K.N. Kudin, J.C. Burant, J.M. Millam, S.S. Iyengar, J. Tomasi, V. Barone, B. Mennucci, M. Cossi, G. Scalmani, N. Rega, G.A. Petersson, H. Nakatsuji, M. Hada, M. Ehara, K. Toyota, R. Fukuda, J. Hasegawa, M. Ishida, T. Nakajima, Y. Honda, O. Kitao, H. Nakai, M. Klene, X. Li, J.E. Knox, H.P. Hratchian, J.B. Cross, C. Adamo, J. Jaramillo, R. Gomperts, R.E. Stratmann, O. Yazyev, A.J. Austin, R. Cammi, C. Pomelli, J.W. Ochterski, P.Y. Ayala, K. Morokuma, G.A. Voth, P. Salvador, J.J. Dannenberg, V.G. Zakrzewski, S. Dapprich, A.D. Daniels, M.C. Strain, O. Farkas, D.K. Malick, A.D. Rabuck, K. Raghavachari, J.B. Foresman, J.V. Ortiz, Q. Cui, A.G. Baboul, S. Clifford, J. Cioslowski, B.B. Stefanov, G. Liu, A. Liashenko, P. Piskorz, I. Komaromi, R.L. Martin, D.J. Fox, T. Keith, M.A. Al-Laham, C.Y. Peng, A. Nanayakkara, M. Challacombe, P.M.W. Gill, B. Johnson, W. Chen, M.W. Wong, C. Gonzalez, and J.A. Pople Gaussian, Revision E.01 2004 Gaussian Wallingford, CT
15. Y. Zhao, and D.G. Truhlar Acc. Chem. Res. 41 2008 157 167
16. C.A. Brandt, A.C.M.P. da Silva, C.G. Pancote, C.L. Brito, and M.A.B. da Silveira Synthesis 2004 1557 1559