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(1) For reviews on the acetalisation reaction see: (a) Meskens, A. J. Synthesis 1981, 501.
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(c) Schmitz, E. Kocienski, P. J. Protective Groups, GT Verlag: Stuttgart-New York, 1994. For acetalation promoted by Lewis acid catalysts see:
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(h) Ishihara, K.; Karumi, Y.; Kubota, M.; Yamamoto, H. Synlett. 1996, 839 and references quoted therein.
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See ref. 1a
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(4) (a) See ref. 1a.
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(d) Bell, J. M.; Kubler, D. G.; Sartwell, P.; Zepp, R. G. J. Org. Chem. 1965, 30, 4284.
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See ref. 9c, pp 42-55
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(b) See ref. 9c, pp 42-55.
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(c) Ogata, J.; Kawasaki, A; Okumura, N. J. Org. Chem. 1964, 29, 1985.
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85038539235
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note
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4-assisted addition of nucleophiles to dimethyl and cyclic acetals.
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34
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84985057411
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(9) Schnurrenberger, P.; Zuger, M. F., Seebach, D. Helv. Chim. Acta 1982, 65, 1197.
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(11) The simplified cycle of Scheme neglects dimeric or aggregated forms of titanium complex: see Reetz, M. T. Organotitanium Reagents in Organic Chemistry, Springer Verlag: Berlin, 1986; p 45.
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Reetz, T.M.1
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85038541551
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note
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N1 -active.
-
-
-
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38
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0010314117
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(13) Many organic compounds of titanium are known to be rapidly hydrolysed in the presence of even traces of water. Joda showed that the catalytic activity of these polymeric derivatives is nearly identical to that of the initial alkoxytitanates. Joda, K. Chem. Soc. Jpn (Ind. Chem. Sect.) 1971, 74, 1476. See also Siling, M. S.; Laricheva, T. N. Russian Chem. Rev. 1996, 65, 279.
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Joda, K.1
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39
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0000260433
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(13) Many organic compounds of titanium are known to be rapidly hydrolysed in the presence of even traces of water. Joda showed that the catalytic activity of these polymeric derivatives is nearly identical to that of the initial alkoxytitanates. Joda, K. Chem. Soc. Jpn (Ind. Chem. Sect.) 1971, 74, 1476. See also Siling, M. S.; Laricheva, T. N. Russian Chem. Rev. 1996, 65, 279.
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Siling, M.S.1
Laricheva, T.N.2
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40
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0000036220
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3 is kinetikally rather labile and this lability would secure the efficiency of chlorotitanium alkoxide as a catalyst: see Gau, H. M.; Lee, C. S.; Lin, C. C.; Jang, M. K.; Ho, Y. C.; Kuo, C. N. J. Am. Chem. Soc. 1996, 118, 2936.
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41
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0010395318
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(15) For each known compound of Table the revelant reference is reported in succession. 1: commercial product, supplier Aldrich; 2: commercial product, supplier Fluka; 3: Box, V.; Hollingsworth, R.; Roberts, E. Heterocycles 1980, 14, 1733;
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Box, V.1
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8: Boate, D. R., Johnston, L. J.; Kwong, P. C.; Lee-Ruff; E.; Scaiano, J. C. J. Am. Chem. Soc. 1990, 112, 8858;
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13: Ghosh, C., Bandyopadhyay, C., Tewari, N. J. Org. Chem. 1984, 49, 2812;
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17: commercial product, supplier Aldrich;
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