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Volumn 9, Issue 7, 2007, Pages 1183-1185

Diastereoselective lower rim (1S)-camphorsulfonylation as the shortest way to the inherently chiral calix[4]arene

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EID: 34147155244     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol0628513     Document Type: Article
Times cited : (56)

References (36)
  • 1
    • 0004268367 scopus 로고    scopus 로고
    • For reviews, see: a, Stoddart, J. F, Ed, The Royal Society of Chemistry: Cambrige
    • For reviews, see: (a) Gutsche, C. D. Calixarenes Revisited; Stoddart, J. F., Ed.; The Royal Society of Chemistry: Cambrige, 1998.
    • (1998) Calixarenes Revisited
    • Gutsche, C.D.1
  • 2
    • 0004287470 scopus 로고    scopus 로고
    • Asfari, Z, Bohmer, V, Harowfield, J, Vicens, J, Eds, Kluwer Academic Publishers; Dordrecht
    • (b) Calixarenes 2001; Asfari, Z., Bohmer, V., Harowfield, J., Vicens, J., Eds.; Kluwer Academic Publishers; Dordrecht, 2001.
    • (2001) Calixarenes 2001
  • 13
    • 0001391127 scopus 로고    scopus 로고
    • For general reviews on chiral calixarenes, see:, Gokel, G, Ed, JAI Press: Stanford
    • For general reviews on chiral calixarenes, see: Vysotsky, M. O.; Schmidt, C.; Bohmer, V. In Advances in Supramolecular Chemistry; Gokel, G., Ed.; JAI Press: Stanford, 2000; Vol. 7, pp 139-233.
    • (2000) Advances in Supramolecular Chemistry , vol.7 , pp. 139-233
    • Vysotsky, M.O.1    Schmidt, C.2    Bohmer, V.3
  • 19
    • 0032568264 scopus 로고    scopus 로고
    • In the case of acetylation of tris(hydroxyethyl)calix[4]arenes with vinyl acetate using lipases as catalysts, a 100% enantiomeric excess of monoacetylated product was achieved with 19% yield. Browne, J. K, McKervey, M. A, Pitarch, M, Russell, J. A, Millership, J. S. Tetrahedron Lett. 1998, 39, 1787
    • (a) In the case of acetylation of tris(hydroxyethyl)calix[4]arenes with vinyl acetate using lipases as catalysts, a 100% enantiomeric excess of monoacetylated product was achieved with 19% yield. Browne, J. K.; McKervey, M. A.; Pitarch, M.; Russell, J. A.; Millership, J. S. Tetrahedron Lett. 1998, 39, 1787.
  • 20
    • 33748967953 scopus 로고    scopus 로고
    • Assymetric induction was also applied for the synthesis of inherently chiral calix[4]arenes in high yields. Boyko, V. I.; Shivanyuk, A.; Pirozhenko, V. V.; Zubatyuk, R. I.; Shiskin, O. V.; Kalchenko. V. I. Tetrahedron Lett. 2006, 47, 7775.
    • (b) Assymetric induction was also applied for the synthesis of inherently chiral calix[4]arenes in high yields. Boyko, V. I.; Shivanyuk, A.; Pirozhenko, V. V.; Zubatyuk, R. I.; Shiskin, O. V.; Kalchenko. V. I. Tetrahedron Lett. 2006, 47, 7775.
  • 33
    • 34147125944 scopus 로고    scopus 로고
    • 26-Monoisopropoxy-25,27,28-trihydroxycalix[4]arene was synthesized according to the litetrature but with sodium methylate (10% excess) as the base and a 5-fold excess of isopropyliodide. The reaction time was 15 h. The yield of compound 1 was 65, Groenen, L. C, Ruël, B. H. M, Casnati, A, Verboom, W, Pochini, A, Ungaro, R, Reinhoudt, D. N. Tetrahedron 1991, 47, 8379
    • 26-Monoisopropoxy-25,27,28-trihydroxycalix[4]arene was synthesized according to the litetrature but with sodium methylate (10% excess) as the base and a 5-fold excess of isopropyliodide. The reaction time was 15 h. The yield of compound 1 was 65%. Groenen, L. C.; Ruël, B. H. M.; Casnati, A.; Verboom, W.; Pochini, A.; Ungaro, R.; Reinhoudt, D. N. Tetrahedron 1991, 47, 8379.
  • 34
    • 34147117241 scopus 로고    scopus 로고
    • It is well known that the reactions performed in the presence of mild bases give exceptionally 1,3-disubstituted products, whereas 1,2-disubstituted products could be obtained with strong bases. For example, see: (a) Van Loon, J. D.; Arduini, A.; Coppi, L.; Verboom, W.; Rochini, A.; Ungaro, R.; Harkema, S.; Reinhoudt, D. N. J. Org. Chem. 1990, 55, 5639.
    • It is well known that the reactions performed in the presence of mild bases give exceptionally 1,3-disubstituted products, whereas 1,2-disubstituted products could be obtained with strong bases. For example, see: (a) Van Loon, J. D.; Arduini, A.; Coppi, L.; Verboom, W.; Rochini, A.; Ungaro, R.; Harkema, S.; Reinhoudt, D. N. J. Org. Chem. 1990, 55, 5639.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.