Synthesis of configurationally defined sexi-and octinaphthalene derivatives

Organic Letters

Volumn 3, Issue 2, 2001, Pages 169-171

  Fuji, Kaoru ^a   Furuta, Takumi ^a   Tanaka, Kiyoshi ^a,b  

^a KYOTO UNIVERSITY   (Japan)

^b UNIVERSITY OF SHIZUOKA   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0001001058     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol006843c     Document Type: Article

References (23)

1. For an extensive review, see: (a) Pu. L. Chem. Rev. 1998, 98, 2405-2494.
2. (b) Martin, R. E.; Diederich F. Angew. Chem., Int. Ed. 1999, 38, 1350-1377.
3. (c) Berresheim, A. J.; Muller, M.; Müllen, K. Chem. Rev. 1999, 99, 1747-1786.
4. Weiss, L. A.; Sakai, N.; Ghebremariam, B.; Ni, C.; Matile, S. J. Am. Chem, Soc. 1997, 119, 12142-12149.
5. (a) Baumeister, B.; Matile, S. Chem. Eur. J. 2000, 6, 1739-1749.
6. (b) Baumeister, B.; Sakai, N.; Matile, S. Angew. Chem., Int. Ed. 2000, 39, 1955-1958.
7. (c) Baumeister, B.; Matile, S. Chem. Commun. 2000, 913-914.
8. (d) Winum, J.-Y.; Matile, S. J. Am. Chem. Soc. 1999, 121, 7961-7962.
9. Cristofaro, M. F.; Chamberlin, A. R. J. Am. Chem. Soc. 1994, 116, 5089-5098.
10. Tour, J. M. Adv. Mater. 1994, 6, 190-198.
11. Hide, F.; Diaz-Garcia, M. A.; Schwartz, B. J.; Heeger, A. J. Acc. Chem. Res. 1997, 30, 430-436.
12. Galda, P.; Rehahn, M. Synthesis 1996, 614-620.
13. Liess, P.; Hensel, V.; Schlüter, A.-D. Liebigs Ann. 1996, 1037-1040.
14. Koch, K.-H.; Müllen, K. Chem. Ber. 1991, 124, 2091-2100.
15. A 9-mer of naphthalene connected at 1,5-positions was reported. See: Marin, G. H.; Horak, V. J. Org. Chem. 1994, 59, 4267-4271.
16. Fuji, K.; Furuta, T.; Otsubo, T.; Tanaka, K.; Tetrahedron Lett. 1999, 7, 3001-3004.
17. Tanaka, K.; Furuta, T.; Fuji, K.; Miwa, Y.; Taga, T.; Tetrahedron: Asymmetry 1996, 7, 2199-2202.
18. (a) Brussee, J.; Groenendijk, J. L. G.; Te Koppele J. M.; Jansen, A. C. A. Tetrahedron 1985, 41, 3313-3319.
19. (b) Hovorka, M.; Scigel, R.; Gunterová, J.; Tichy, M.; Závada, J. Tetrahedron 1992, 48, 9503-9516.
20. (c) Smrcina, M.; Polákova, J.; Vyskocil, S.; Kocovsky, P. J. Org. Chem. 1993, 58, 4534-4538.
21. (d) Noji, M.; Nakajima, M.; Koga, K.; Tetrahedron Lett. 1994, 35, 7983-7984.
22. 2. After addition of 2 N HCl to decompose the copper-amine complex the mixture was condensed under reduced pressure. Extractive workup followed by preparative TLC gave 16 (27 mg), 17 (24 mg), 12 (66 mg), and its isomer with S,R,S-configuration (51 mg).
23. This type of helix was called a Geländer-type molecule. See: Kiupel, B.; Niederalt, C.; Nieger, M.; Grimme, S.; Vögtle, F. Angew. Chem., Int. Ed. 1998, 37, 3031-3034.