Regio- and stereo-selective aza-Diels-Alder reaction of ethyl glyoxylate 4-methoxyphenylimine with 1,3-dienes in the presence of BF3·Et2O. Evidence for a non-concerted mechanism

Tetrahedron

Volumn 63, Issue 3, 2007, Pages 727-734

  Alves, M José ^a   Azoia, Nuno G ^a   Fortes, A Gil ^a  

^a UNIVERSITY OF MINHO   (Portugal)

Author keywords

2 Azadienes; Diels Alder cycloaddition; Glyoxylate arylimines

Indexed keywords

1,7 BIS 2 (TERT BUTYLDIMETHYLSILYLOXY)VINYL] 9 METHOXY 1,2,3,4,5,6,7 HEXAHYDROPYRIDO[3,2,1 IJ]QUINOLINE 3,5 DICARBOXYLATE; ALKADIENE; ETHYL 3 (TERT BUTYLDIMETHYLSILYLOXY) 4 [2 (TERT BUTYLDIMETHYLSILOXY) VINYL] 6 METHOXY 3,4 DIHYDROQUINOLINE 2 CARBOXYLATE; ETHYL 3 ACETOXY 4 [(2 ACETOXY) VINYL] 6 METHOXY 1,2,3,4 TETRAHYDROQUINOLINE 2 CARBOXYLATE; ETHYL 6 METHOXY 3 METHYL 4 (PROP 1 ENYL) 1,2,3,4 TETRAHYDROQUINOLINE 2 CARBOXYLATE; ETHYL 6 METHOXY 3 PHENYL 4 STYRYL 1,2,3,4 TETRAHYDROQUINOLINE 2 CARBOXYLATE; ETHYL 6 METHOXY 4 (2 METHOXYVINYL) 1,2,3,4 TETRAHYDROQUINOLINE 2 CARBOXYLATE; ETHYL 6 METHOXY 4 (2 OXOETHYL) 1,2,3,4 TETRAHYDROQUINOLINE 2 CARBOXYLATE; ETHYL 6 METHOXYQUINOLINE 2 CARBOXYLATE; ETHYL [2 (TERT BUTYLDIMETHYLSILYLOXY)VINYL] 6 METHOXY 1,2,3,4 TETRAHYDROQUINOLINE 2 CARBOXYLATE; ETHYL GLYOXYLATE 4 METHOXYPHENYLIMINE; IMINE; QUINOLINE DERIVATIVE; TETRAHYDROQUINOLINE;

ARTICLE; CHEMICAL REACTION; CYCLOADDITION; DRUG MECHANISM; DRUG SYNTHESIS; ISOMER; PRIORITY JOURNAL; STEREOCHEMISTRY; SUBSTITUTION REACTION;

BETULACEAE;

EID: 33845322646     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2006.10.085     Document Type: Article

References (29)

1. Katritzky A.R., Rachwal S., and Rachwal B. Tetrahedron 52 (1996) 15031-15070
2. U.S. Patent 0,087,926 A1, 2003.
3. Boger D.L., and Weinreb S.M. Hetero Diels-Alder Methodology in Organic Synthesis (1987), Academic, San Diego Chapters 2 and 9
4. Weinreb S.M. In: Trost B.M., and Fleming I. (Eds). Comprehensive Organic Synthesis Vol. 5 (1991), Pergamon, Oxford 401-449
5. Crousse B., Bégué J.-P., and Bonnet-Delpon D. J. Org. Chem. 65 (2000) 5009-5013
6. Yadav J.S., Reddy B.V.S., Gayathri K.U., and Prasad A.R. Synthesis (2002) 2537-2541
7. Zhang J., and Li C.-J. J. Org. Chem. 67 (2002) 3969-3971
8. Batey R.A., Powell D.A., Acton A., and Lough A.L. Tetrahedron Lett. 42 (2001) 7935-7939
9. Di Salvo A., Spanedda M.V., Ourévich M., Crousse B., and Bonnet-Delpon D. Synthesis (2003) 2231-2235
10. Babu G., and Perumal P.T. Tetrahedron Lett. 38 (1997) 5025-5026
11. Babu G., and Perumal P.T. Tetrahedron Lett. 39 (1998) 3225-3228
12. Kobayashi S., Ishitani H., and Nagayama S. Synthesis (1995) 1195-1202
13. Borrione E., Prato M., Scorrano G., and Stivanello M. J. Heterocycl. Chem. 25 (1988) 1831-1835
14. Leeson P.D., Carling R.W., Moore K.W., Moseley A.M., Smith J.D., Stevenson G., Chan T., Bakar R., Foster A.C., Grimwood S., Kemp J.A., Marshall G.R., and Hoogsteen K. J. Med. Chem. 35 (1992) 1954-1968
15. Stevenson G., Leeson P.D., Rowley M., Sanderson I., and Stansfield I. Bioorg. Med. Chem. Lett. 2 (1992) 371-374
16. Nagarajam R., and Perumal P.T. Synth. Commun. (2001) 1733-1736
17. Lucchini V., Prato M., Scorrano G., and Tecilla P. J. Org. Chem. 53 (1988) 2251-2258
18. Hermitage S., Howard J.A.K., Prichard D.J.R.G., Probert M.R., and Whiting A. Org. Biomol.Chem. 2 (2004) 2451-2460
19. Hermitage S., Jay D., and Whiting A. Tetrahedron Lett. 43 (2002) 9633-9636
20. Alves M.J., Almeida I.G., Fortes A.G., and Freitas A.P. Tetrahedron Lett. 44 (2003) 6561-6565
21. Grieco P.A., and Bahsas A. Tetrahedron Lett. 29 (1988) 5855-5858
22. Crystallographic data (excluding structure factors) for the structures in this paper have been deposited with the Cambridge Crystallographic Data Centre as supplementary publication nos. CCDC 622654 (compound 15c) and 622655 (compound 5a). Copies of the data can be obtained, free of charge, on application to CCDC, 12 Union Road, Cambridge CB2 1EZ, UK (fax: +44 1223 336033 or e-mail: deposit@ccdc.cam.ac.uk).
23. Kiselyov A., and Armstrong R.W. Tetrahedron Lett. 38 (1997) 6163-6166
24. Prato M., Scorrano G., Stivanello M., and Tecilla P. Gazz. Chim. Ital. 117 (1987) 325-326
25. Talukdar S., Chao-Tsen C., and Jim-Min F. J. Org. Chem. 65 (2000) 3148-3153
26. Talukdar S., Rong-Jium C., Chao-Tsen C., Le-Chiang L., and Jim-Min F. J. Comb. Chem. 3 (2001) 341-345
27. Chen D., Zhou J., Saiah E., and Beaton G. Org. Lett. 4 (2002) 4411-4414
28. Ward Y.C., Villanueva L.A., Allred G.D., and Liebeskind L.S. J. Am. Chem. Soc. 118 (1996) 897-898
29. Jia X., Lin H., Huo C., Zhang W., Lü J., Yang L., Zhao G., and Liu Z. Synlett (2003) 1707-1709