Palladium-Catalyzed Reactions: Stereoselective Synthesis of Substituted Cyclopropanes Related to Chrysanthemic Acid. A Simple Route to cis -Chrysanthemonitrile

Journal of Organic Chemistry

Volumn 46, Issue 11, 1981, Pages 2414-2417

  Genet, Jean Pierre ^a   Piau, Frederique ^a  

^a SORBONNE UNIVERSITÉ   (France)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0343874418     PISSN: 00223263     EISSN: 15206904     Source Type: Journal    
DOI: 10.1021/jo00324a049     Document Type: Article

References (21)

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2. “Methoden dei Organischen Chemie (Houben-Weyl)”; Georg Thieme Verlag: Stuttgart, 1952; Band IV/3, p 94.
3. Review: Synthetic Pyrethroid. A new class of insecticide. Eliott, M.; Janes, N. F. Chem. Rev. 1979, 473.
4. For a preliminary report of this work see: Genet, J. P.; Piau, F.; Ficini, J. Tetrahedron Lett. 1980, 21, 3183.
5. Julia, S.; Julia, M.; Linstrumelle, G. Bull. Soc. Chim. Fr. 1966, 3499.
6. Reviews: (a) Trost, B. M. Tetrahedron 1977,33, 2615;
7. Trost, B. M. Pure Appl. Chem. 1979,51,787;
8. Trost, B. M. Acc. Chem. Res. 1980,13,385;
9. “Organic Synthesis with Palladium Compounds”; Tsuji, J., Ed. Springer Verlag: West Berlin and Heidelberg, 1979;
10. Tsuji, J. Pure Appl. Chem. 1979, 51, 1235.
11. Barreau, B.; Boat, H.; Julia, M.; Lallemand, J. Y. Tetrahedron Lett. 1975, 40, 1975.
12. Trost, B. M.; Klun, T. P. J. Am. Chem. Soc. 1979, 101, 6756.
13. For a discussion of regioselectivity of alkylation on-aUylpaliadium complexes, see: Trost, B. M.; Weber, L.; Strege, P. E.; Fullerton, T. J.; Dietshe, T. J. J. Am. Chem. Soc. 1978,100, 3420; Trost, B. M.; Verhoeven, T. R. J. Am. Chem. Soc. 1980, 102, 4730.
14. For an intermolecular process using an allylic alcohol and a palladium catalyst, see: Atkins, K. E.; Walker, W. E.; Manyik, R. M. Tetrahedron Lett. 1970, 43, 3821.
15. Steglisch, W.; Hofle, G. Angew. Chem., Int. Ed. Engl. 1969,8,98. See also a review: Hofle, G.; Steglisch, W.; Verbruggen, H. Tetrahedron Lett. 1978, 17, 569.
16. For a recent observation of this type in the chrysanthemic series, see: Lindsay, R. J.; Ferguson, I.; Costello, A. T.; Thomas, A. (Imperial Chemical Industries Ltd.) German Patent 2 751610; British Appl. 76/ 48078; Chem. Abstr. 1978, 89, 108333.
17. The hydrogenation of 3 on Pd/CaC03 gave ds-dihydrochrysanthemonitrile. 4 We express sincere thanks to Professor M. Julia and Dr. Linstrumelle for copies of NMR spectra of cis-and trans-dihydrochrysanthemonitrile.
18. Pascali, V.; Umani-Ronchi, A. J. Chem. Soc., Chem. Commun. 1973,351.
19. Julia, M. “7th International Symposium on Organic Sulfur Chemistry”, Tiller, A., Ed.; Potoroz, Yugoslavia, 1978; p 121.
20. Coulson, D. R. Inorg. Synth. 1972, 13, 121.
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