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For N-BOC protection, see: Greene, T. W.; Wuts, P. G. M. Protective Group in Organic Synthesis, 3rd ed.; Wiley: New York, 1999; pp 518-525. For O-BOC protection, see: (a) Houlihan, F.; Bouchard, F.; Fréchet, J. M. J.; Willson, C. G. Can. J. Chem. 1985, 63, 153. (b) Losse, G.; Süptitz, G. Synthesis 1990, 1035.
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For N-BOC protection, see: Greene, T. W.; Wuts, P. G. M. Protective Group in Organic Synthesis, 3rd ed.; Wiley: New York, 1999; pp 518-525. For O-BOC protection, see: (a) Houlihan, F.; Bouchard, F.; Fréchet, J. M. J.; Willson, C. G. Can. J. Chem. 1985, 63, 153. (b) Losse, G.; Süptitz, G. Synthesis 1990, 1035.
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For N-BOC protection, see: Greene, T. W.; Wuts, P. G. M. Protective Group in Organic Synthesis, 3rd ed.; Wiley: New York, 1999; pp 518-525. For O-BOC protection, see: (a) Houlihan, F.; Bouchard, F.; Fréchet, J. M. J.; Willson, C. G. Can. J. Chem. 1985, 63, 153. (b) Losse, G.; Süptitz, G. Synthesis 1990, 1035.
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0342408321
-
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note
-
This differs from the reaction of amines and alcohols with simple carboxylic acid anhydrides (for alcohols, see, for instance, ref 2d).
-
-
-
-
18
-
-
0342843250
-
-
note
-
All ratios and yields in this work are based on NMR integration unless otherwise is mentioned.
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19
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0343713578
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note
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Details for best conditions to obtain various products are found in the footnotes of each table.
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For protection of diols, see: (a) De Angelis, F.; Marzi, M.; Minetti, P.; Misiti, D.; Muck, S. J. Org. Chem 1997, 62, 4159 and references therein. (b) Greene, T. W.; Wuts, P. G. M. Protective Group in Organic Synthesis; Wiley: New York; 3rd ed.; 1999; pp 201-245.
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For protection of diols, see: (a) De Angelis, F.; Marzi, M.; Minetti, P.; Misiti, D.; Muck, S. J. Org. Chem 1997, 62, 4159 and references therein. (b) Greene, T. W.; Wuts, P. G. M. Protective Group in Organic Synthesis; Wiley: New York; 3rd ed.; 1999; pp 201-245.
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For conversion of diols to cyclic carbonates by other methods see: (a) Burk, R. M.; Roof M. B. Tetrahedron Lett. 1993, 34, 395. (b) Cotarca, L.; Delogu, P.; Nardelli, A.; Sunjic', V. Synthesis 1996, 553. (c) Nicolaou, K. C.; Claiborne, C. F.; Nantermet, P. G.; Couladouros, E. A.; Sorensen E. J. J. Am. Chem. Soc. 1994, 116, 1591.
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For conversion of diols to cyclic carbonates by other methods see: (a) Burk, R. M.; Roof M. B. Tetrahedron Lett. 1993, 34, 395. (b) Cotarca, L.; Delogu, P.; Nardelli, A.; Sunjic', V. Synthesis 1996, 553. (c) Nicolaou, K. C.; Claiborne, C. F.; Nantermet, P. G.; Couladouros, E. A.; Sorensen E. J. J. Am. Chem. Soc. 1994, 116, 1591.
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