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0026012210
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For several examples on asymmetric reactions with D-serinal (2), see: Michael-type addition: Jako, I.; Uiber, P.; Mann, A.; Wermuth, C.-G.; Boulanger, T.; Norberg, B.; Evrard, G.; Durant, F. J. Org. Chem. 1991, 56, 5729.
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[3+2] Cycloaddition: Raghaven, S.; Ishida, M.; Shinozaki, H.; Nakanishi, K.; Ohfune, Y. Tetrahedron Lett. 1993, 34, 5765.
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Avenoza, A.; Cativiela, C.; Fernández-Recio, M.A.; Peregrina, J.M. Tetrahedron: Asymmetry 1996, 7, 721.
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Avenoza, A.; Cativiela, C.; Peregrina, J.M.; Zurbano, M.M. Tetrahedron: Asymmetry 1997, 8, 863.
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0027980535
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Sodium borohydride was used instead of lithium borohydride, but a decrease in the yield was then observed. Meffre, P. Durand, P.; Branquet, E.; le Goffic, F. Synth. Commun. 1994, 24, 2147.
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Williams, L.1
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34547391096
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note
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3.
-
-
-
-
36
-
-
34547390196
-
-
note
-
Another protective group (tert-butyldimethylsilyl) for the hydroxy substituent of L-serine (3) was tested. This group could not be used in the total synthesis of 2 since it caused several problems in the formation of the oxazolidine ring due to the action of an acid medium, which produced hydrolysis of the O-Si bond.
-
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37
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12644312578
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Mancuso, A.J.; Huang, S.-L.; Swern, D. J. Org. Chem. 1978, 43, 2480.
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0001582498
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0001649196
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Dhaon, M.K.; Olsen, R.K.; Ramasamy, K. J. Org. Chem. 1982, 47, 1962.
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34547390233
-
-
note
-
Duplication of some signals in the NMR spectra was observed due to nitrogen inversion.
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