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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
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(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.
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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.
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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
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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.
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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.
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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.
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