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79955776433
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Monofunctionlization of diols, triols and polyols using peptide-based catalysts has been reported; see
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Monofunctionlization of diols, triols and polyols using peptide-based catalysts has been reported; see
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22
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33748581386
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24
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79955754873
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Hydrogen-bonding based selectivity using peptide-based catalysts has been reported; see
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Hydrogen-bonding based selectivity using peptide-based catalysts has been reported; see
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25
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0032564916
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S. J. Miller, G. T. Copeland, N. Papaioannou, T. E. Horstmann, E. M. Ruel, J. Am. Chem. Soc. 1998, 120, 1629-1630
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28
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85050296727
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The equation was generated by modifying an equation for the selectivity factor of kinetic resolution; see.
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The equation was generated by modifying an equation for the selectivity factor of kinetic resolution; see:, H. B. Kagan, J. C. Fiaud, Top. Stereochem. 1988, 18, 249-331.
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29
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79955770251
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+=C substructure because of the reported X-ray structure of several N-acyl-4-dialkylaminopydinium ions; see
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+=C substructure because of the reported X-ray structure of several N-acyl-4-dialkylaminopydinium ions; see
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30
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84918255664
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P. G. Jones, K. Linoh, A. Z. Blaschette, Z. Naturforsch. B 1990, 45, 267
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B. Tao, J. C. Ruble, D. A. Hoic, G. C. Fu, J. Am. Chem. Soc. 1999, 121, 5091.
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35
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79955783179
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2-symmetry. The stereoview of the calculated structure A was shown in the Supporting Information.
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2-symmetry. The stereoview of the calculated structure A was shown in the Supporting Information.
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36
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79955767989
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The distance between the two oxygen atoms of the extended conformation of 1,6-hexanediol is estimated to be 7.3Å by molecular modeling. The sum (10.0Å) of 7.3Å and the hydrogen-bonding distance (2.7Å) seems too long for effective molecular recognition by acylpyridinium ion A. This could be the reason of poor selectivity of monoacylation of diols such as 1,6-hexanediol and 1,7-heptanediol. In contrast, acylation of diols having a chain length shorter than five atoms proceeds with high selectivity for monoacylation. The effective distance (7.3Å) shown in Figure2 b is expected to be adjustable and therefore shortened by the bond rotation around C2-CO(NHR).
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The distance between the two oxygen atoms of the extended conformation of 1,6-hexanediol is estimated to be 7.3Å by molecular modeling. The sum (10.0Å) of 7.3Å and the hydrogen-bonding distance (2.7Å) seems too long for effective molecular recognition by acylpyridinium ion A. This could be the reason of poor selectivity of monoacylation of diols such as 1,6-hexanediol and 1,7-heptanediol. In contrast, acylation of diols having a chain length shorter than five atoms proceeds with high selectivity for monoacylation. The effective distance (7.3Å) shown in Figure2 b is expected to be adjustable and therefore shortened by the bond rotation around C2-CO(NHR).
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37
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79955763196
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The predominant formation of the monoacylate 2 a (2 a / 3 a =3.5) by DMAP-catalysis observed in entry8 in Table2 is assumed to be due to the initial low concentration of 2 a in the reaction medium and low conversion (37 % recovery of 1 a).
-
The predominant formation of the monoacylate 2 a (2 a / 3 a =3.5) by DMAP-catalysis observed in entry8 in Table2 is assumed to be due to the initial low concentration of 2 a in the reaction medium and low conversion (37 % recovery of 1 a).
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38
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79955770037
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Specific rate acceleration in acylation by peptide-based catalysts has been reported; see
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Specific rate acceleration in acylation by peptide-based catalysts has been reported; see
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39
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0033596302
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E. R. Jarvo, G. T. Copeland, N. Paparioannou, P. J. Bonitatebus, Jr., S. J. Miller, J. Am. Chem. Soc. 1999, 121, 11638-11643
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Jarvo, E.R.1
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Miller, S.J.5
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41
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79955783594
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Direct monoacylation of linear diols may be useful in the preparation of insect pheromones and hybrid esters, see
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Direct monoacylation of linear diols may be useful in the preparation of insect pheromones and hybrid esters, see
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44
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79955748672
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reference[3a].
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reference[3a].
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