Facile preparation of novel nonracemic oxy-substituted cyclopropanone S,S-acetals by γ-cyclisation of glyceric aldehyde dithioacetal derivatives and studies of their reactivity

Liebigs Annales

Volumn , Issue 7, 1997, Pages 1447-1452

  Schwarz, Hans Georg ^a   Dreeßen, Sylvia ^a   Tersakian, Ani ^b   Schaumann, Ernst ^a  

^a CLAUSTHAL UNIVERSITY OF TECHNOLOGY   (Germany)

^b UNIVERSITY OF ALEPPO   (Syrian Arab Republic)

Author keywords

Burgess' reagent; Carbanions, sulfur stabilized; Cyclopropanone S,S acetals; Glyceric aldehyde dithioacetals; Nonracemic cyclopropanes; Cyclizations

Indexed keywords

EID: 0009580198     PISSN: 09473440     EISSN: None     Source Type: Journal    
DOI: 10.1002/jlac.199719970723     Document Type: Article

References (31)

1. Methods of Org. Chem. (Houben-Weyl) 4th ed. 1952-1996 (Ed.: A. De Meijere), vol. E17a, Thieme, Stuttgart, 1996;
2. B. Halton, M. G. Banwell, The Chemistry of the Cyclopropyl Group (Ed.: Z. Rappoport), vol. 2, John Wiley & Sons Ltd., New York, 1987.
3. M. Pohmakotr, A. Takampon, J. Ratchataphusit, Tetrahedron 1996, 52, 7149-7158.
4. P. Binger, P. Wedemann, R. Goddard, U. H. Brinker J. Org. Chem. 1996, 61, 6462-6464;
5. D. L. Boger, C. E. Brotherton, G. I. Georg, Org. Synth. 1987, 65, 32-41;
6. A. Weber, M. Neuenschwander, Angew. Chem. 1981, 93, 790-791;
7. Angew. Chem. Int Ed. Engl. 1981, 20, 774-775.
8. D. L. Boger, C. E. Brotherton-Pleiss, Advances in Cycloaddition; Ed.: D. P. Curran, vol. 2, JAI Press, Greenwich, CT, 1990;
9. D. L. Boger, C. E. Brotherton, J. Am. Chem. Soc. 1984, 106, 805-807.
10. H.-G. Schwarz, E. Schaumann, J. Chem. Soc., Perkin Trans. 1 1996, 2773-2776.
11. G. Guanti, L. Banfi, E. Narisano, Tetrahedron Lett. 1986, 27, 3547-3550.
12. H. J. Bestmann, B. Pecher, Synthesis 1991, 731-734.
13. T. Sato, M. Nakakita, S. Kimura, T. Fujisawa, Tetrahedron Lett. 1989, 30, 977-981.
14. Y. Gao, R. M. Hanson, J. M. Klunder, S. Y. Ko, H. Masamune, K. B. Sharpless, J. Am. Chem. Soc. 1987, 109, 5765-5780.
15. C. A. M. Afonso, M. T. Barros, L. S. Godhino, C. D. Maycock, Synthesis 1991, 575-580;
16. K. Saigo, Y. Hashimoto, L. Fang, M. Hasegawa, Heterocycles 1989, 29, 2079-2082;
17. Z. Sui, P. S. Furth, J. J. de Voss, J. Org. Chem. 1992, 57, 6658-6662;
18. F. Bellesia, M. Boni, F. Ghelfi, U. M. Pagnoni, Tetrahedron 1993, 49, 199-206;
19. A. Nickon, A. D. Rodriguez, V. Shirhatti, R. Ganguly, J. Org. Chem. 1985, 50, 4218-4226.
20. D. B. Grotjahn, N. H. Andersen, J. Chem. Soc., Chem. Commun. 1981, 306-307.
21. Apparatus see: E. Schaumann, J. Ehlers, H. Mrotzek, Liebigs Ann. Chem. 1979, 1734-1745.
22. E. M. Burgess, H. R. Penton Jr., E. A. Taylor, J. Org. Chem. 1973, 38, 26-31.
23. H. Yamaguchi, K. Kawada, T. Okamoto, E. Egert, H. J. Lindner, M. Braun, R. Dammann, M. Liesner, H. Neumann, D. Seebach, Chem. Ber. 1976, 109, 1589-1600;
24. K. Banert, Chem. Ber. 1985, 118, 1564-1574;
25. E. Vilsmaier, S. Weber, J. Weidner, J. Org. Chem. 1987, 52, 4921-4924.
26. A. Weber, U. Stämpfli, M. Neuenschwander, Helv. Chim. Acta 1989, 72, 29-40.
27. W. E. Parham, W. D. McKnown, V. Nelson, S. Kajigaeshi, N. Ishikawa, J. Org. Chem. 1973, 38, 1361-1365;
28. M. Fedorynski, A. Dybowska, A. Jonczyk, Synthesis 1988, 549-551.
29. P. Shi-Qi, E. Winterfeldt, Liebigs Ann. Chem. 1989, 1045-1047.
30. D. Seebach, M. Kolb, B.-T. Gröbel, Chem. Ber. 1973, 106, 2277-2290.
31. D. Villemin, B. Labiad, Synth. Commun. 1992, 22, 2043-2052.