A Novel Strategy for the Synthesis of Molecules with Helical Chirality. Intramolecular [2 + 2 + 2] Cycloisomerization of Triynes under Cobalt Catalysis

Journal of Organic Chemistry

Volumn 63, Issue 12, 1998, Pages 4046-4050

  Stará, Irena G ^a   Starý, Ivo ^a   Kollárovič, Adrian ^a   Teplý, Filip ^a   Šaman, David ^a   Tichý, Miloš ^a  

^a INSTITUTE OF ORGANIC CHEMISTRY AND BIOCHEMISTRY   (Czech Republic)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0001747974     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo9801263     Document Type: Article

References (27)

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2. For reviews on helicenes, see: (a) Vögtle, F. Fascinating Molecules in Organic Chemistry; Wiley: New York, 1992; p 156. (b) Meurer, K. P.; Vögtle, F. Top. Curr. Chem. 1985, 127, 1. (c) Laarhoven, W. H.; Prinsen, W. J. C. Top. Curr. Chem. 1984, 125, 63. (d) Martin, R. H. Angew. Chem. 1974, 86, 727. (e) Wynberg, H. Acc. Chem. Res. 1970, 4, 65.
3. For reviews on helicenes, see: (a) Vögtle, F. Fascinating Molecules in Organic Chemistry; Wiley: New York, 1992; p 156. (b) Meurer, K. P.; Vögtle, F. Top. Curr. Chem. 1985, 127, 1. (c) Laarhoven, W. H.; Prinsen, W. J. C. Top. Curr. Chem. 1984, 125, 63. (d) Martin, R. H. Angew. Chem. 1974, 86, 727. (e) Wynberg, H. Acc. Chem. Res. 1970, 4, 65.
4. For reviews on helicenes, see: (a) Vögtle, F. Fascinating Molecules in Organic Chemistry; Wiley: New York, 1992; p 156. (b) Meurer, K. P.; Vögtle, F. Top. Curr. Chem. 1985, 127, 1. (c) Laarhoven, W. H.; Prinsen, W. J. C. Top. Curr. Chem. 1984, 125, 63. (d) Martin, R. H. Angew. Chem. 1974, 86, 727. (e) Wynberg, H. Acc. Chem. Res. 1970, 4, 65.
5. For reviews on helicenes, see: (a) Vögtle, F. Fascinating Molecules in Organic Chemistry; Wiley: New York, 1992; p 156. (b) Meurer, K. P.; Vögtle, F. Top. Curr. Chem. 1985, 127, 1. (c) Laarhoven, W. H.; Prinsen, W. J. C. Top. Curr. Chem. 1984, 125, 63. (d) Martin, R. H. Angew. Chem. 1974, 86, 727. (e) Wynberg, H. Acc. Chem. Res. 1970, 4, 65.
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8. Helicene-based chiral ligands have been recently proposed (ref 5) and synthesized (ref 6a). To our best knowledge, only Reetz et al. reported the application of a helicene derivative to enantioselective catalysis (ref 6b).
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16. For procedures that do not use irradiation, see footnotes 1-3 and 6 in ref 12.
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24. Triynes 1-7 are readily accessible by an acetylene-aryl halide coupling methodology. Manuscript in preparation.
25. Kündig, E. P.; Dupré, C.; Bourdin, B.; Cunningham, A., Jr.; Pons, D. Heiv. Chim. Acta 1994, 77, 421 and references therein.
26. Schore N. E. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Paquette, L. A., Eds.; Pergamon Press: Oxford, 1991; Vol. 5, Chapter 9.4, p 1129.
27. The structure of cobalt complexes is under study.