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1
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0002378156
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For a leading reference of asymmetric acylation of alcohols:
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For a leading reference of asymmetric acylation of alcohols: Ichikawa J., Asami M., Mukaiyama T. Chem. Lett. 1984;949.
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(1984)
Chem. Lett.
, pp. 949
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Ichikawa, J.1
Asami, M.2
Mukaiyama, T.3
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5
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0032564916
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Miller S.J., Copeland G.T., Papaioannou N., Horstmann T.E., Ruel E.M. J. Am. Chem. Soc. 120:1998;1629.
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(1998)
J. Am. Chem. Soc.
, vol.120
, pp. 1629
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-
Miller, S.J.1
Copeland, G.T.2
Papaioannou, N.3
Horstmann, T.E.4
Ruel, E.M.5
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10
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0011249788
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Iwasaki F., Maki T., Nakashima W., Onomura O., Matsumura Y. Org. Lett. 1:1999;969.
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(1999)
Org. Lett.
, vol.1
, pp. 969
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-
Iwasaki, F.1
Maki, T.2
Nakashima, W.3
Onomura, O.4
Matsumura, Y.5
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13
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0034700040
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Spivey A.C., Maddaford A., Fekner T., Redgrave A.J., Frampton C.S. J. Chem. Soc., Perkin Trans. 1. 2000;3460.
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(2000)
J. Chem. Soc., Perkin Trans. 1
, pp. 3460
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Spivey, A.C.1
Maddaford, A.2
Fekner, T.3
Redgrave, A.J.4
Frampton, C.S.5
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15
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0035930814
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Kawabata T., Yamamoto K., Momose Y., Yoshida H., Nagaoka Y., Fuji K. Chem. Commun. 2001;2700.
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(2001)
Chem. Commun.
, pp. 2700
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Kawabata, T.1
Yamamoto, K.2
Momose, Y.3
Yoshida, H.4
Nagaoka, Y.5
Fuji, K.6
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17
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0020087653
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Preparation of PPY analogues from proline has been reported, see: (a) Delaney, E. J.; Wood, L. E.; Klotz, I. M. J. Am. Chem. Soc. 1982, 104, 799;
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(1982)
J. Am. Chem. Soc.
, vol.104
, pp. 799
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Delaney, E.J.1
Wood, L.E.2
Klotz, I.M.3
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18
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0037136132
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(b) Priem, G.; Anson, M. S.; Macdonald, S. J. F.; Pelotier, B.; Campbell, I. B. Tetrahedron Lett. 2002, 43, 6001.
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(2002)
Tetrahedron Lett.
, vol.43
, pp. 6001
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Priem, G.1
Anson, M.S.2
Macdonald, S.J.F.3
Pelotier, B.4
Campbell, I.B.5
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19
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0013036507
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For examples, acylative kinetic resolution of racemic-3 catalyzed by 20 and 21 proceeds with selectivity factors of 11 and 1.6, respectively, see Ref. 4.
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For examples, acylative kinetic resolution of racemic-3 catalyzed by 20 and 21 proceeds with selectivity factors of 11 and 1.6, respectively, see Ref. 4.
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20
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0033596302
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It has been reported that N-methylimidazole analogues with peptide side chains effectively promote asymmetric acylation and phosphorylation of alcohols, see: (a) Jarvo, E. R.; Copeland, G. T.; Papaioannou, N.; Bonitatebus, P. J., Jr.; Miller, S. J. J. Am. Chem. Soc. 1999, 121, 11638;
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(1999)
J. Am. Chem. Soc.
, vol.121
, pp. 11638
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Jarvo, E.R.1
Copeland, G.T.2
Papaioannou, N.3
Bonitatebus P.J., Jr.4
Miller, S.J.5
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21
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0037010024
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(b) Sculimbrene, B. R.; Morgan, A. J.; Miller, S. J. J. Am. Soc. Chem. 2002, 124, 11653.
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(2002)
J. Am. Soc. Chem.
, vol.124
, pp. 11653
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Sculimbrene, B.R.1
Morgan, A.J.2
Miller, S.J.3
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22
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0013031496
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While 1,5-disubsituted imidazoles are known to be active nucleophilic catalysts (Ref. 7), 1,4-disubsituted surrogates are not.
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While 1,5-disubsituted imidazoles are known to be active nucleophilic catalysts (Ref. 7), 1,4-disubsituted surrogates are not.
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25
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0012942196
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For examples, acylative kinetic resolution of racemic-3 with isobutyric anhydride was promoted by 5 mol% of 8, 9, and 10 to give (1S, 2R)-3 in 88% ee at 68% conversion (s=6.3), in 83% ee at 67% conversion (s=5.6), and in 99% ee at 78% conversion (s=7.6), respectively.
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For examples, acylative kinetic resolution of racemic-3 with isobutyric anhydride was promoted by 5 mol% of 8, 9, and 10 to give (1S, 2R)-3 in 88% ee at 68% conversion (s=6.3), in 83% ee at 67% conversion (s=5.6), and in 99% ee at 78% conversion (s=7.6), respectively.
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-
-
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26
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0013031580
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note
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+), found m/z 619.2875.
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27
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0001272372
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For an example of enzymatic desymmetrization of meso-1,3-cyclohexanediol, see:
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For an example of enzymatic desymmetrization of meso-1,3-cyclohexanediol, see: Mattson A., Orrenius C., Oehrner N., Unelius C.R., Hult K., Norin T. Acta Chem. Scand. 50:1996;918.
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(1996)
Acta Chem. Scand.
, vol.50
, pp. 918
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Mattson, A.1
Orrenius, C.2
Oehrner, N.3
Unelius, C.R.4
Hult, K.5
Norin, T.6
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28
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0002658793
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For examples of nonenzymatic acylative desymmetrization of meso-diols, see: (a) Terashima, S.; Yamada, S. Tetrahedron Lett. 1977, 18, 1001;
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(1977)
Tetrahedron Lett.
, vol.18
, pp. 1001
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Terashima, S.1
Yamada, S.2
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32
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0032554989
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Also see Ref. 2a
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(e) Oriyama, T.; Imai, K.; Sano, T.; Hosoya, T. Tetrahedron Lett. 1998, 39, 3529. Also see Ref. 2a.
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(1998)
Tetrahedron Lett.
, vol.39
, pp. 3529
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Oriyama, T.1
Imai, K.2
Sano, T.3
Hosoya, T.4
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33
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0012942197
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R=65, 67 min.
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R=65, 67 min.
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34
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0012935174
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Similar cooperative effect, albeit less significant, was observed in the acylation of 14 with 10 in toluene: Kinetic resolution of racemic-15 with 10 in toluene gave recovered 15 in 18% ee at 47% conversion (s=1.8) whose absolute configuration was same as that obtained by mono-acylation of 14 with 10.
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Similar cooperative effect, albeit less significant, was observed in the acylation of 14 with 10 in toluene: Kinetic resolution of racemic-15 with 10 in toluene gave recovered 15 in 18% ee at 47% conversion (s=1.8) whose absolute configuration was same as that obtained by mono-acylation of 14 with 10.
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