First synthesis, isolation and characterization of enantiomerically pure and inherently chiral resorc[4]arenes by lewis acid cyclization of a resorcinol monoalkyl ether

European Journal of Organic Chemistry

Volumn , Issue 8, 2003, Pages 1404-1409

  Klaes, Michael ^a   Agena, Ceno ^a   Köhler, Markus ^a   Inoue, Maki ^b   Wada, Takehiko ^b   Inoue, Yoshihisa ^b   Mattay, Jochen ^a  

^a BIELEFELD UNIVERSITY   (Germany)

^b OSAKA UNIVERSITY   (Japan)

Author keywords

Asymmetric synthesis; Chirality; Circular dichroism; Monofunctionalization; Resorc 4 arenes

Indexed keywords

ALKYL GROUP; CAMPHOR DERIVATIVE; ETHER DERIVATIVE; LEWIS ACID; POLYCYCLIC AROMATIC HYDROCARBON DERIVATIVE; RESORCINOL DERIVATIVE; SOLVENT;

ARTICLE; CHEMICAL STRUCTURE; CHIRALITY; CHROMATOGRAPHY; CIRCULAR DICHROISM; CYCLIZATION; DIASTEREOISOMER; ENANTIOMER; ISOMER; RACEMIC MIXTURE; REACTION ANALYSIS; STEREOISOMERISM; STRUCTURE ANALYSIS; SYNTHESIS;

EID: 0038032750     PISSN: 1434193X     EISSN: None     Source Type: Journal    
DOI: 10.1002/ejoc.200390197     Document Type: Article

References (16)

1. L. M. Tunstad, J. A. Tucker, E. Dalcanale, J. Weiser, J. A. Byrant, J. C. Sherman, R. C. Helgeson, C. B. Knobler, D. J. Cram, J. Org. Chem. 1989, 54, 1305-1312.
2. P. Timmerman, W. Verboom, D. N. Reinhoudt, Tetrahedron 1996, 52, 2663-2704.
3. W. Iwanek, R. Fröhlich, M. Urbaniak, C. Näther, J. Mattay, Tetrahedron 1998, 54, 14031-14040.
4. I. Schlachter, U. Höweler, W. Iwanek, M. Urbaniak, J. Mattay, Tetrahedron 1999, 55, 14931-14940.
5. M. C. Letzel, C. Agena, J. Mattay, J. Mass Spectrometry 2002, 37, 63-68.
6. W. Iwanek, J. Mattay, Liebigs Ann. 1995, 1463-1466.
7. R. Arnecke, V. Böhmer, S. Friebe, S. Gebauer, G. J. Krauss, I. Thondorf, W. Vogt, Tetrahedron Lett. 1995, 36, 6221-6224.
8. U. Schneider, H.-J. Schneider, Chem. Ber. 1994, 127, 2455-2469.
9. W. Iwanek, C. Wolff, J. Mattay, Tetrahedron Lett. 1995, 36, 8969-8972.
10. Y. Matsushita, T. Matsui, Tetrahedron Lett. 1993, 34, 7433-7436.
11. P. C. Bulman Page, H. Heaney, E. P. Sampler, J. Am. Chem. Soc. 1999, 121, 6751-6752.
12. C. Agena, C. Wolff, J. Mattay, Eur. J. Org. Chem. 2001, 2977-2981.
13. M. J. McIldowie, M. Mocerino, B. W. Skelton, A. H. White, Org. Lett. 2000, 2, 3869-3871.
14. 4 symmetrical resorc[4]arenes has not yet been investigated.
15. 1H NMR spectroscopy. The slightly different isolated yields are due to the separation by HPLC.
16. S. Kim, J. Sohn, S. Y. Park, Bull. Korean Chem. Soc. 1999, 20, 473-477.