Synthesis of chiral condensed S-heterocycles via stereoselective Michael-like addition to butenolides and α,β-unsaturated lactams

Tetrahedron

Volumn 52, Issue 27, 1996, Pages 9035-9046

  Faltz, Heike ^b   Bohrisch, Jörg ^b   Wohlauf, Wilko ^b   Pätzel, Michael ^b   Jones, Peter G ^a   Liebscher, Jürgen ^b  

^a TECHNICAL UNIVERSITY OF BRAUNSCHWEIG   (Germany)

^b HUMBOLDT UNIVERSITY   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

FURAN DERIVATIVE; PYRROLE DERIVATIVE; THIOPHENE DERIVATIVE;

ARTICLE; CHIRALITY; DRUG SYNTHESIS; PRIORITY JOURNAL; REACTION ANALYSIS; TECHNIQUE; X RAY CRYSTALLOGRAPHY;

EID: 0342758933     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/0040-4020(96)00458-9     Document Type: Article

References (14)

1. 1. Bohrisch, J., Pätzel, M., Liebscher, J., Jones, P.G. Tetrahedron Lett. 1993, 34, 2749-2752.
2. 2. Bohrisch, J., Faltz, H., Pätzel, M., Liebscher, J. Tetrahedron 1994, 36, 10701-10708.
3. 3. Rudorf, W.-D. in Methoden der Organischen Chemie (Houben Weyl), Kreher, P., Ed.; Thieme, Stuttgart, 1994, Vol. E6a-1, pp. 290-327.
4. 4. Mukaiyama, T. Org. Reactions 1982, 28, 203-331.
5. 5. Aromatic thieno[2.3-c]furans are also scarcely known: Schöning. A., Debaerdemaeker, T., Zander, M., Friedrichsen, W. Chem. Ber. 1989, 122, 1119-1131; Eberbach, W., Laber, N., Bussenius, J., Fritz, H., Rihs, G. Chem. Ber. 1993, 126, 975-995.
6. 5. Aromatic thieno[2.3-c]furans are also scarcely known: Schöning. A., Debaerdemaeker, T., Zander, M., Friedrichsen, W. Chem. Ber. 1989, 122, 1119-1131; Eberbach, W., Laber, N., Bussenius, J., Fritz, H., Rihs, G. Chem. Ber. 1993, 126, 975-995.
7. 6. We could find no partially saturated pyrrolo[3,2-b]-1,4-thiazines, but just one aromatic compound in the literature: Okafor, C. O., Akpuaka, M. U. J. Chem. Soc. Perkin Trans. 1 1993, 159-161.
8. 7. For a review see: Hiemstra, H., Speckamp, W. N. In Comprehensive Organic Synthesis, Trost, B. M., Flemming, I., Eds.; Pergamon Press, Oxford, 1991, Vol. 2, pp. 1047-1082.
9. 8. 1a: Thiele, J., Tischbein, R., Lossow, E. Ann. Chemie 1901, 319, 180-195;
10. 1b: Häfele, B., Jäger, V. Liebigs Ann. Chem. 1987, 85-87;
11. 1c: Ikota, N. Chem. Pharm. Bull. 1992, 40, 1925-1927;
12. 1d: Romo, P., Romina, I., Midura, W., Meyers, A. I. Tetrahedron 1990, 46, 4951-4994.
13. 9. Further investigation of the cyclization of the adduct 3a to 6a revealed that the diastereselectivity can be enhanced if the reaction was performed in dioxane at 5°C followed by stirring at room temperature for 24h.
14. 10. Full details of the structure determination have been deposited at the Fachinformationszentrum Karlsruhe, Gesellschaft für Wissenschaftlich-technische Information mbH, D-76344 Eggenstein-Leopoldshafen, Germany. Any request for this material should quote a full literature citation and the reference number CSD 405097 (for 7a) and 405098 (for 16).