Unprecedented regio- and stereoselective conversion of 1-cyclopropyl-3- ethoxycyclopentadienes to 3-(E)-alkylidenecyclopentenes

Journal of Organic Chemistry

Volumn 64, Issue 2, 1999, Pages 400-404

  Flynn, Bernard L ^a,b   De Meijere, Armin ^a  

^a UNIVERSITY OF GÖTTINGEN   (Germany)

^b AUSTRALIAN NATIONAL UNIVERSITY   (Australia)

Author keywords

[No Author keywords available]

Indexed keywords

1 CYCLOPROPYL 3 ETHOXYCYCLOPENTADIENE DERIVATIVE; ALCOHOL; CYCLOPENTADIENE DERIVATIVE; CYCLOPENTENE DERIVATIVE; TETRAHYDROFURAN; UNCLASSIFIED DRUG;

ARTICLE; CATALYSIS; COMPLEX FORMATION; HYDROLYSIS; STEREOCHEMISTRY; STEREOISOMERISM; SYNTHESIS;

EID: 0033593545     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo980938z     Document Type: Article

References (43)

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10. Cf. (a) Small Ring Compounds in Organic Synthesis I-V; de Meijere, A., Ed.; Topics in Current Chemistry; Springer: Berlin, Heidelberg, 1986, 1987, 1988, 1990, 1996; Vols. 133, 135, 144, 155, 178. (b) Reissig, H.-U. in The Chemistry of the Cyclopropyl Group; Rappoport, Z., Ed.; Wiley: Chichester, New York, 1987; p 375 ff. (c) Salaün, J. Chem. Rev. 1983, 83, 619. (d) Wong, H. N. C.; Hon, M.-Y.; Tse, C.-W.; Yip, Y.-C.; Tanko, J.; Hudlicky, T. Chem. Rev. 1989, 89, 165. (e) de Meijere, A.; Wessjohann, L. Synlett 1990, 20. (f) de Meijere, A. in New Aspects of Organic Chemistry II, Yoshida, Z.-i., Ohshiro, Y., Eds.; Kodansha: Tokyo, 1992; p 181 ff.
11. Cf. (a) Small Ring Compounds in Organic Synthesis I-V; de Meijere, A., Ed.; Topics in Current Chemistry; Springer: Berlin, Heidelberg, 1986, 1987, 1988, 1990, 1996; Vols. 133, 135, 144, 155, 178. (b) Reissig, H.-U. in The Chemistry of the Cyclopropyl Group; Rappoport, Z., Ed.; Wiley: Chichester, New York, 1987; p 375 ff. (c) Salaün, J. Chem. Rev. 1983, 83, 619. (d) Wong, H. N. C.; Hon, M.-Y.; Tse, C.-W.; Yip, Y.-C.; Tanko, J.; Hudlicky, T. Chem. Rev. 1989, 89, 165. (e) de Meijere, A.; Wessjohann, L. Synlett 1990, 20. (f) de Meijere, A. in New Aspects of Organic Chemistry II, Yoshida, Z.-i., Ohshiro, Y., Eds.; Kodansha: Tokyo, 1992; p 181 ff.
12. Cf. (a) Small Ring Compounds in Organic Synthesis I-V; de Meijere, A., Ed.; Topics in Current Chemistry; Springer: Berlin, Heidelberg, 1986, 1987, 1988, 1990, 1996; Vols. 133, 135, 144, 155, 178. (b) Reissig, H.-U. in The Chemistry of the Cyclopropyl Group; Rappoport, Z., Ed.; Wiley: Chichester, New York, 1987; p 375 ff. (c) Salaün, J. Chem. Rev. 1983, 83, 619. (d) Wong, H. N. C.; Hon, M.-Y.; Tse, C.-W.; Yip, Y.-C.; Tanko, J.; Hudlicky, T. Chem. Rev. 1989, 89, 165. (e) de Meijere, A.; Wessjohann, L. Synlett 1990, 20. (f) de Meijere, A. in New Aspects of Organic Chemistry II, Yoshida, Z.-i., Ohshiro, Y., Eds.; Kodansha: Tokyo, 1992; p 181 ff.
13. Cf. (a) Small Ring Compounds in Organic Synthesis I-V; de Meijere, A., Ed.; Topics in Current Chemistry; Springer: Berlin, Heidelberg, 1986, 1987, 1988, 1990, 1996; Vols. 133, 135, 144, 155, 178. (b) Reissig, H.-U. in The Chemistry of the Cyclopropyl Group; Rappoport, Z., Ed.; Wiley: Chichester, New York, 1987; p 375 ff. (c) Salaün, J. Chem. Rev. 1983, 83, 619. (d) Wong, H. N. C.; Hon, M.-Y.; Tse, C.-W.; Yip, Y.-C.; Tanko, J.; Hudlicky, T. Chem. Rev. 1989, 89, 165. (e) de Meijere, A.; Wessjohann, L. Synlett 1990, 20. (f) de Meijere, A. in New Aspects of Organic Chemistry II, Yoshida, Z.-i., Ohshiro, Y., Eds.; Kodansha: Tokyo, 1992; p 181 ff.
14. Cf. (a) Small Ring Compounds in Organic Synthesis I-V; de Meijere, A., Ed.; Topics in Current Chemistry; Springer: Berlin, Heidelberg, 1986, 1987, 1988, 1990, 1996; Vols. 133, 135, 144, 155, 178. (b) Reissig, H.-U. in The Chemistry of the Cyclopropyl Group; Rappoport, Z., Ed.; Wiley: Chichester, New York, 1987; p 375 ff. (c) Salaün, J. Chem. Rev. 1983, 83, 619. (d) Wong, H. N. C.; Hon, M.-Y.; Tse, C.-W.; Yip, Y.-C.; Tanko, J.; Hudlicky, T. Chem. Rev. 1989, 89, 165. (e) de Meijere, A.; Wessjohann, L. Synlett 1990, 20. (f) de Meijere, A. in New Aspects of Organic Chemistry II, Yoshida, Z.-i., Ohshiro, Y., Eds.; Kodansha: Tokyo, 1992; p 181 ff.
15. Cf. (a) Small Ring Compounds in Organic Synthesis I-V; de Meijere, A., Ed.; Topics in Current Chemistry; Springer: Berlin, Heidelberg, 1986, 1987, 1988, 1990, 1996; Vols. 133, 135, 144, 155, 178. (b) Reissig, H.-U. in The Chemistry of the Cyclopropyl Group; Rappoport, Z., Ed.; Wiley: Chichester, New York, 1987; p 375 ff. (c) Salaün, J. Chem. Rev. 1983, 83, 619. (d) Wong, H. N. C.; Hon, M.-Y.; Tse, C.-W.; Yip, Y.-C.; Tanko, J.; Hudlicky, T. Chem. Rev. 1989, 89, 165. (e) de Meijere, A.; Wessjohann, L. Synlett 1990, 20. (f) de Meijere, A. in New Aspects of Organic Chemistry II, Yoshida, Z.-i., Ohshiro, Y., Eds.; Kodansha: Tokyo, 1992; p 181 ff.
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26. (b) Flynn, B. L.; Silveira, C. C.; de Meijere, A. Synlett 1995, 812.
27. (c) Flynn, B. L.; Funke, F. J.; Noltemeyer, M.; de Meijere, A. Tetrahedron 1995, 57, 11141.
28. We have taken advantage of a similar transient chromium-complexed cycloadduct in the migration of double bonds and the addition of water to the alternative carbonyl-inserted [2 + 2 + 1] cycloadducts. Cf. loc. cit. (10b).
29. The recently developed reaction conditions are highly selective for the formation of 5-dialkylamino-3-ethoxycyclopentadienes from the cycloaddition of alkynes even to 3-(dimethylamino)-2-propenylidene chromium complexes not bearing a cyclopropyl group at the C3 position. Cf. loc. cit. (7).
30. For reviews on the Dötz reaction, see: (a) Dötz, K. H. Angew. Chem. 1984, 96, 573; Angew. Chem., Int. Ed. Engl. 1984, 23, 587. (b) Wulff, W. D.; Tang, P.-C.; Chan, K.-S.; McCallum, J. S.; Yang, D. C.; Gilbertson, S. R. Tetrahedron 1985, 41, 5813.
31. For reviews on the Dötz reaction, see: (a) Dötz, K. H. Angew. Chem. 1984, 96, 573; Angew. Chem., Int. Ed. Engl. 1984, 23, 587. (b) Wulff, W. D.; Tang, P.-C.; Chan, K.-S.; McCallum, J. S.; Yang, D. C.; Gilbertson, S. R. Tetrahedron 1985, 41, 5813.
32. For reviews on the Dötz reaction, see: (a) Dötz, K. H. Angew. Chem. 1984, 96, 573; Angew. Chem., Int. Ed. Engl. 1984, 23, 587. (b) Wulff, W. D.; Tang, P.-C.; Chan, K.-S.; McCallum, J. S.; Yang, D. C.; Gilbertson, S. R. Tetrahedron 1985, 41, 5813.
33. 1H NMR spectrum of the crude reaction mixture (obtained by evaporation of the solvent acetonitrile) only revealed resonances attributable to 11 and triphenylphosphane oxide. The incomplete mass balance of this reaction is attributed to the partial decomposition of 11 upon workup or chromatography.
34. N2″ is based on the fact that the triphenylphosphane/ bromine reagent normally substitutes alcohols in a concerted manner: Wiley G. A.; Rein, B. M.; Hershkowitz R. L. Tetrahedron Lett. 1964, 2509. However, this assignment is tentative, and the proof of concertedness of this reaction will require further investigation.
35. (a) Wijnberg J. B. P. A.; Wiering, P. G.; Stenberg, H. Synthesis 1981, 901.
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39. In unsubstituted vinylcyclopropane, the conformational equilibrium is between a synclinal (gauche) and an antiperiplanar (s-trans) conformer with the latter predominating: de Meijere, A.; Lüttke, W. Tetrahedron 1969, 25, 2047. Traetteberg, M.; Bakken, P.; Almenningen, A.; Lüttke, W. J. Mol. Struct. 1988, 189, 357.
40. In unsubstituted vinylcyclopropane, the conformational equilibrium is between a synclinal (gauche) and an antiperiplanar (s-trans) conformer with the latter predominating: de Meijere, A.; Lüttke, W. Tetrahedron 1969, 25, 2047. Traetteberg, M.; Bakken, P.; Almenningen, A.; Lüttke, W. J. Mol. Struct. 1988, 189, 357.
41. 2β-unsaturated ketones occurs selectively in a 1,4-mode: Casey C. P.; Cesa, M. C. J. Am. Chem. Soc. 1979, 101, 4236.
42. 2β-unsaturated ketones occurs selectively in a 1,4-mode: Casey C. P.; Cesa, M. C. J. Am. Chem. Soc. 1979, 101, 4236.
43. 2β-unsaturated ketones occurs selectively in a 1,4-mode: Casey C. P.; Cesa, M. C. J. Am. Chem. Soc. 1979, 101, 4236.