Enantioselective synthesis of Epi-emetine analogues: Control of the facial selectivity in a three-component domino Knoevenagel-hetero-Diels-Alder reaction

Zeitschrift fur Naturforschung - Section B Journal of Chemical Sciences

Volumn 59, Issue 4, 2004, Pages 468-477

  Tietze, Lutz F ^a   Rackelmann, Nils ^a  

^a UNIVERSITY OF GÖTTINGEN   (Germany)

Author keywords

Alkaloids; Bischler Napieralski Reaction; Domino Reactions; Enantioselective Hydrogenation; Iminium Ions; Multicomponent Reactions

Indexed keywords

ALKALOIDS; CONDENSATION; HYDROGENATION; REACTION KINETICS; SOLVENTS;

BISCHLER-NAPIERALSKI REACTION; DOMINO REACTIONS; ENANTIOSELECTIVE HYDROGENATION; IMINIUM IONS; MULTI-COMPONENT REACTIONS;

ENANTIOSELECTIVITY;

ALDEHYDE; EMETINE; ETHER; PHENETHYLAMINE; QUINOLIZIDINE DERIVATIVE;

CATALYST; CHIRALITY; CONFERENCE PAPER; DIASTEREOISOMER; DIELS ALDER REACTION; ENANTIOSELECTIVITY; HYDROGENATION; HYDROGENOLYSIS; POLYMERIZATION; SOLVOLYSIS; SYNTHESIS;

EID: 2442451179     PISSN: 09320776     EISSN: None     Source Type: Journal    
DOI: 10.1515/znb-2004-0415     Document Type: Conference Paper

References (21)

1. a) L. F. Tietze, U. Beifuß, Angew. Chem. 105, 137 (1993); Angew. Chem. Int. Ed. 32, 131 (1993);
2. a) L. F. Tietze, U. Beifuß, Angew. Chem. 105, 137 (1993); Angew. Chem. Int. Ed. 32, 131 (1993);
3. b) L. F. Tietze, Chem. Rev. 96, 115 (1996);
4. c) L. F. Tietze, A. Modi, Medicinal Research Reviews 4, 304 (2000);
5. d) L.F. Tietze, F. Haunert, in F. Vögtle, J.F. Stoddart, M. Shibasaki (eds): Stimulating Concepts in Chemistry, p. 40-64, Wiley-VCH, Weinheim (2000);
6. e) G. Appendino, G. Cravotto, A. Minassi, Eur. J. Org. Chem. 3711 (2001);
7. f) G. Cravotto, G. M. Nano, G. Palmisano, S. Tagliapietra, Tetrahedron: Asymmetry, 12, 707 (2001);
8. g) B. B. Snider, Q. Lu, J. Org. Chem 61, 2839 (1996).
9. a) L.F. Tietze, J. Bachmann, J. Wichmann, O. Burkhardt, Synthesis 1185 (1994);
10. b) L.F. Tietze, H. Evers, E. Töpken, Angew. Chem. 40, 903 (2001); Angew. Chem. Int. Ed. 113, 927 (2001).
11. b) L.F. Tietze, H. Evers, E. Töpken, Angew. Chem. 40, 903 (2001); Angew. Chem. Int. Ed. 113, 927 (2001).
12. a) L. F. Tietze, J. Bachmann, J. Wichmann, Y. Zhou, T. Raschke, Liebigs Ann./Recueil 881 (1997);
13. b) L. F. Tietze, Y. Zhou, Angew. Chem. 111, 2076 (1999); Angew. Chem. Int. Ed. Engl. 38, 2045 (1999).
14. b) L. F. Tietze, Y. Zhou, Angew. Chem. 111, 2076 (1999); Angew. Chem. Int. Ed. Engl. 38, 2045 (1999).
15. L. F. Tietze, N. Rackelmann, I. Müller, Chem. Eur. J. (2004) in press.
16. L. F. Tietze, H. Evers, E. Töpken, Helv. Chim. Acta 85, 4200 (2002).
17. L. F. Tietze, N. Rackelmann, G. Sekar, Angew. Chem. 115, 4386 (2003); Angew. Chem. Int. Ed. Engl. 42, 4254 (2003).
18. L. F. Tietze, N. Rackelmann, G. Sekar, Angew. Chem. 115, 4386 (2003); Angew. Chem. Int. Ed. Engl. 42, 4254 (2003).
19. A.C. Cheng, N. Castagnoli, J. Med. Chem. 27, 513 (1984).
20. A. Basha, M. Lipton, S. M. Weinreb, Tetrahedron Lett. 18, 4171 (1977).
21. N. Uematsu, A. Fujii, S. Hashiguchi, T. Ikariya, R. Noyori, J. Am. Chem. Soc. 118, 4916 (1996).