Diastereoselective cycloadditions of new trifluoromethyl azomethine ylides derived from trifluorothioacetamides

Tetrahedron Letters

Volumn 37, Issue 31, 1996, Pages 5515-5518

  Laduron, Frédéric ^a   Ates, Célal ^a   Viehe, Heinz G ^a  

^a UNIVERSITÉ CATHOLIQUE DE LOUVAIN   (Belgium)

Author keywords

[No Author keywords available]

Indexed keywords

PYRROLIDINE DERIVATIVE; PYRROLIZINE DERIVATIVE;

ARTICLE; DRUG SYNTHESIS; NUCLEAR MAGNETIC RESONANCE; REACTION ANALYSIS; STEREOCHEMISTRY;

EID: 0030605899     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/0040-4039(96)01185-9     Document Type: Article

References (15)

1. 1. Depending on their substituents, dehydrochlorination or dehaloalkylation are well documented: a) Bonnett, R. in The Chemisny of the Carbon-Nitrogen Double Bonds, Pataï Ed.; Interscience, New York 1970, Chapter 13;
2. b) Ulrich, H. in The Chemistry of Imidoyl Halides, Plenum Press, New York 1968, Chapter 3;
3. c) Kantlehner, W. in Iminium salts in organic chemistry, Part 2; Böhme H. and Viehe H.G. Eds.; Wiley Interscience, New York 1976, p. 118.
4. 2. a) Huys, F.; Merényi, R.; Janousek, Z.; Stella, L.; Viehe, H. G. Angew. Chem. Int. Ed. Engl. 1979, 18, 615-616;
5. b) Viehe, H. G.; Merényi, R.; Janousek, Z. Pure & Appl. Chem. 1988, 60, 1635-1644;
6. c) Viehe, H. G.; Janousek, Z.; Merényi, R. in Free Radicals in Synthesis and Biology; Minisci F. Ed.; Kluwer Academic Publishers 1989. pp. 1-26 and references cited therein.
7. 3. a) Fishwick, C. W. G.; Foster, R. J.; Carr, R. E. Tetrahedron Lett. 1996, 37, 711-714;
8. b) Fishwick, C. W. G.; Foster, R. J.; Carr, R. E. Tetrahedron Lett. 1995, 36, 9409-9412;
9. c) Magedov, I.; Kornienko, A. V.; Zotova, T. O.; Drozd, V. N. Tetrahedron Lett. 1995, 36, 4619-4622;
10. d) Katritzky, A. R.; Zhu, L.; Lang, H.; Denisko, O.; Wang, Z. Tetrahedron 1995, 51, 13271-13276 and references cited therein.
11. 4. The formation of 4 via 2 or 3 and the related rearrangement studies will be published separately.
12. 5. Other cyclic amino derivatives are currently being studied.
13. 10 in excellent yields.
14. 7. Tinant, B.; Declercq, J. P.; Laduron, F.; Viehe, H. G.; to be published separately.
15. 3): 5a: -66.8, 5b: -68.2, 9a: -70.4, 9b: -76.5, 10a: -71.5, 10b: -75.7, 11a: -68.1, 11b: -71.8 ppm.