Collect. Czech. Chem. Commun.
2006, 71, 1256-1264
https://doi.org/10.1135/cccc20061256
Modified Synthesis of Heptahelicene and Its Resolution Into Single Enantiomers
Zuzana Alexandrováa, Petr Sehnala, Irena G. Staráa,*, Ivo Starýa,*, David Šamana, Stephen G. Urquhartb and Edwige Oterob
a Center for Biomolecules and Complex Molecular Systems, Institute of Organic Chemistry and Biochemistry, Academy of Sciences of the Czech Republic, Flemingovo nám. 2, 166 10 Prague 6, Czech Republic
b Department of Chemistry, University of Saskatchewan, Saskatoon SK S7N 5C9, Canada
References
1. O., Carravetta V., Vahtras O., Agren H.: Chem. Phys. 1998, 232, 49.
<https://doi.org/10.1016/S0301-0104(98)00055-X>
2. S., Zema N., Zennaro S., Alagna L., Stewart B., Peacock R. D., Prosperi T.: J. Am. Chem. Soc. 2004, 126, 4532.
<https://doi.org/10.1021/ja039348v>
3. G., Viefhaus J., Cvejanović S., Rolles D., Gessner O., Lischke T., Hentges R., Wienberg C., Mahler W., Becker U., Langer B., Prosperi T., Zema N., Turchini S., Zada B., Senf F.: Phys. Rev. A: At., Mol., Opt. Phys. 2004, 69, 062717.
<https://doi.org/10.1103/PhysRevA.69.062717>
4a. A.: Angew. Chem., Int. Ed. 2003, 42, 3986.
<https://doi.org/10.1002/anie.200301667>
4b. Hopf H.: Classics in Hydrocarbon Chemistry: Syntheses, Concepts, Perspectives, p. 323. VCH, Weinheim 2000.
4c. T. J.: Angew. Chem., Int. Ed. 2000, 39, 1921.
<https://doi.org/10.1002/1521-3773(20000602)39:11<1921::AID-ANIE1921>3.0.CO;2-F>
4d. G., Seiffert U., Janecka A.: Chem.-Ztg. 1987, 111, 69.
4e. Vögtle F.: Fascinating Molecules in Organic Chemistry, p. 156. Wiley, New York 1992.
4f. K. P., Vögtle F.: Top. Curr. Chem. 1985, 127, 1.
<https://doi.org/10.1007/BFb0049438>
4g. W. H., Prinsen W. J. C.: Top. Curr. Chem. 1984, 125, 63.
<https://doi.org/10.1007/3-540-13569-3_3>
5. R. H., Marchant M. J.: Tetrahedron 1974, 30, 349.
6a. R., Ben Hassine B., Genet J.-P., Gorsane M., Marinetti A.: Eur. J. Org. Chem. 2004, 1517.
<https://doi.org/10.1002/ejoc.200300470>
6b. A., Katz T. J.: Tetrahedron Lett. 1986, 27, 2231.
<https://doi.org/10.1016/S0040-4039(00)84494-9>
6c. M., Nasielski J., Martin R. H.: Tetrahedron Lett. 1967, 8, 743.
<https://doi.org/10.1016/S0040-4039(00)90586-0>
7a. S. K., Grandbois A., Vachon M. P., Cote J.: Angew. Chem., Int. Ed. 2006, 45, 2923.
<https://doi.org/10.1002/anie.200504150>
7b. F., Stará I. G., Starý I., Kollárovič A., Šaman D., Rulíšek L., Fiedler P.: J. Am. Chem. Soc. 2002, 124, 9175.
<https://doi.org/10.1021/ja0259584>
7c. M., Dubois F.: Tetrahedron Lett. 1999, 40, 1309.
<https://doi.org/10.1016/S0040-4039(98)02670-7>
8a. K., Hidehira Y., Takahashi K., Hiyama T., Nozaki K.: Angew. Chem., Int. Ed. 2005, 44, 7136.
<https://doi.org/10.1002/anie.200502855>
8b. M. C., Gonzalez-Lopez M., Urbano A.: Chem. Commun. 2005, 611.
<https://doi.org/10.1039/b413879a>
8c. M., Rajca A., Pink M., Rajca S.: Chem. Eur. J. 2004, 10, 6531.
<https://doi.org/10.1002/chem.200400635>
8d. W. J., Calvin M., Buchardt O.: J. Am. Chem. Soc. 1972, 94, 494.
<https://doi.org/10.1021/ja00757a029>
9a. T., Paruch K., Katz T. J., Rheingold A. L., Lam K.-C., Liable-Sands L.: J. Org. Chem. 2000, 65, 1850.
<https://doi.org/10.1021/jo9919411>
9b. K., Katz T. J., Incarvito C., Lam K.-C., Rhatigan B., Rheingold A. L.: J. Org. Chem. 2000, 65, 7602.
<https://doi.org/10.1021/jo001055m>
10. R. H., Marchant M. J.: Tetrahedron 1974, 30, 343.
<https://doi.org/10.1016/S0040-4020(01)91468-1>
11a. T., Urakawa A. Behzadi B., Ernst K.-H., Baiker A.: New J. Chem. 2004, 28, 332.
<https://doi.org/10.1039/b312877f>
11b. Y. H., Tishbee A., Gil-Av E.: J. Am. Chem. Soc. 1980, 102, 5915.
<https://doi.org/10.1021/ja00538a040>
11c. F., Boshart G.: J. Chromatogr. 1978, 149, 455.
<https://doi.org/10.1016/S0021-9673(00)81004-3>
11d. C. H., Ryall R. R.: J. Chromatogr. 1978, 150, 511.
<https://doi.org/10.1016/S0021-9673(00)88211-4>
12a. I. G., Alexandrová Z., Teplý F., Sehnal P., Starý I., Šaman D., Buděšínský M., Cvačka J.: Org. Lett. 2005, 7, 2547.
<https://doi.org/10.1021/ol047311p>
12b. F., Stará I. G., Starý I., Kollárovič A., Šaman D., Fiedler P., Vyskočil Š.: J. Org. Chem. 2003, 68, 5193.
<https://doi.org/10.1021/jo034369t>
12c. I. G., Starý I., Kollárovič A., Teplý F., Šaman D., Fiedler P.: Collect. Czech. Chem. Commun. 2003, 68, 917.
<https://doi.org/10.1135/cccc20030917>
12d. I. G., Starý I., Kollárovič A., Teplý F., Vyskočil Š., Šaman D.: Tetrahedron Lett. 1999, 40, 1993.
<https://doi.org/10.1016/S0040-4039(99)00099-4>
12e. I. G., Starý I., Kollárovič A., Teplý F., Šaman D., Tichý M.: J. Org. Chem. 1998, 63, 4046.
<https://doi.org/10.1021/jo9801263>
13. I. G., Kollárovič A., Teplý F., Starý I., Šaman D., Fiedler P.: Collect. Czech. Chem. Commun. 2000, 65, 577.
<https://doi.org/10.1135/cccc20000577>
14a. J. K., Jalisatgi S., Matzger A. J., Negrón A., Vollhardt K. P. C.: J. Org. Chem. 1996, 61, 4798.
<https://doi.org/10.1021/jo960143x>
14b. K., Deffense E., Habermann D.: Angew. Chem., Int. Ed. Engl. 1983, 22, 716.
<https://doi.org/10.1002/anie.198307161>
14c. K., Deffense E., Habermann D.: Angew. Chem. Suppl. 1983, 1005.
<https://doi.org/10.1002/anie.198310050>
15. Y., Tanahashi A., Lee S.-Y., Hayashi T.: J. Org. Chem. 1993, 58, 1945.
<https://doi.org/10.1021/jo00059a059>
16. Optical rotation of (–)-(M)-6 published by Martin (ref.10, [α]57925 –5900 ± 200, c 0.06, CHCl3) is substantially higher than the value measured by us, despite the fact that we repeatedly checked the purity of (–)-(M)-6 (purified by HPLC or recrystallized from heptane) by 1H NMR and 13C NMR and enantiopurity by HPLC on a chiral column. The CD spectrum was in full agreement with the literature data.

