Cyanomethylene cyclopropane, a useful dipolarophile and dienophile in [2+3] and [2+4] cycloadditions

Tetrahedron Letters

Volumn 39, Issue 38, 1998, Pages 6857-6860

  Mauduit, Marc ^a   Kouklovsky, Cyrille ^a   Langlois, Yves ^a  

^a CNRS   (France)

Author keywords

[No Author keywords available]

Indexed keywords

3 METHYL 2 BUTENENITRILE; CYANOMETHYLENE CYCLOPROPANE; CYCLOPROPANE; ETHOXYCARBONYLMETHYLENE CYCLOPROPANE; ETHYL 3 METHYL 2 BUTENOATE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL REACTION; CHEMICAL STRUCTURE; REACTION ANALYSIS; STEREOCHEMISTRY; STRUCTURE ANALYSIS; SYNTHESIS;

EID: 0032541687     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(98)01496-8     Document Type: Article

References (17)

1. 1) For a review, see : Langlois, Y.; Pouilhès, A.; Kouklovsky, C.; Morelli, J.-F.; Haudrechy. A.; Kobayakawa, M.; André-Barrès, C.; Berranger, T.; Dirat O. Bull. Soc. Chim. Belg. 1996, 105, 639-657.
2. 2) For a review on asymmetric 1,3 dipolar cycloadditions, see : Gothelf, K. V.; Jorgensen, K.A. Chem. Rev. 1998, 98, 863-903.
3. 3) a) For a review on alkylidenecyclopropane in cycloaddition, see : Goti, A.; Cordero, F. M.; Brandi, A. Top. in Curr. Chem., 1996, 178, 1-98.
4. b) For a recent use of alkylidenecyclopropane as dienophile in intramolecular Diels-Alder reaction see, Heiner, T.; Michalski, S.; Gerke, K.; Buback, M.; de Meijere, A. Synlett, 1995, 355-357 and references there in.
5. 4) For the use of alkylidenecyclopropanes as dienes, see: Thiemann, T.; Kohlstruck, S.; Schwär, G.: de Meijere, A. Tetrahedron Letters, 1991, 32, 3483-3486 and references there in.
6. 5) For a review on the synthesis of alkylidenecyclopropanes, see : Brandi, A.; Goti, A. Chem. Rev. 1998, 98, 589-635.
7. 6) Wilson, C. L. J. Chem. Soc. 1945, 58-61.
8. 7) Spitzner D.; Swoboda, H. Tetrahedron Letters, 1986, 27, 1281-1284.
9. 8) Salaün, J.; Marguerite, J. Org. Synth. 1984, 63, 147-153.
10. 9) Tripett, S.: Walker, D. M. J. Chem. Soc. 1959, 3874-3876.
11. 10) Schiemenz, G. P.; Engelhard. H. Chem. Ber. 1961, 94, 578-585.
12. 11) Novikov, S. S.; Shvekhgeimer, G. A. Izvest. Akad. Nauk. 1960, 2061-2063, (Chem. Abstr. 1961, 13353g). Increasing yield (85%) in the preparation of 6 has been described by these authors, but we have been unable to obtain their results.
13. 11) Novikov, S. S.; Shvekhgeimer, G. A. Izvest. Akad. Nauk. 1960, 2061-2063, (Chem. Abstr. 1961, 13353g). Increasing yield (85%) in the preparation of 6 has been described by these authors, but we have been unable to obtain their results.
14. 13C NMR : 4.22, 5.34, 90.51, 116.95, 152.08.
15. 13) Brandi, A.; Carli, S.; Goti, A. Heterocycles, 1988, 27, 17-20.
16. 1H NMR NOESY experiments. Under thermodynamic conditions whithout Lewis acid, the exo adduct 22 is still the major isomer.
17. 15) For the same cycloaddition between 4b and 15 whithout Lewis acid catalyst, see: Seyed-Mahdavi, F.: Teichmann, S.; de Meijere, A. Tetrahedron Letters, 1986, 27, 1685-1688.