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1. Absolute structure was checked using Friedel pairs and chemical information. CCDC-630533 (3c) contains the supplementary crystallographic data for this paper. These data can be obtained free of charge via www.ccdc-.cam.ac.uk/conts/retrieving.html (or the Cambridge Data Center, 12 Union Road, Cambridge CB21EZ, UK; fax (+44)1223-336.033; or deposit@ccdc.cam.ac.uk).
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1. Absolute structure was checked using Friedel pairs and chemical information. CCDC-630533 (3c) contains the supplementary crystallographic data for this paper. These data can be obtained free of charge via www.ccdc-.cam.ac.uk/conts/retrieving.html (or the Cambridge Data Center, 12 Union Road, Cambridge CB21EZ, UK; fax (+44)1223-336.033; or deposit@ccdc.cam.ac.uk).
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To explain the ring opening of amino epoxides 1 or 2 by other nucleophiles (refs 11-14), a direct attack of the nucleophiles to the oxirane ring, without participation of the dibenzylamino group, was proposed because the reaction took place (under the same reaction conditions) on epoxides without a dibenzylamino group.
-
To explain the ring opening of amino epoxides 1 or 2 by other nucleophiles (refs 11-14), a direct attack of the nucleophiles to the oxirane ring, without participation of the dibenzylamino group, was proposed because the reaction took place (under the same reaction conditions) on epoxides without a dibenzylamino group.
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4544351364
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The selective coordination of the Lewis acid with the epoxide instead of the nitrogen of dibenzylamino group is proposed on the basis of previous results. Thus, the treatment of dibenzylamino aziridines with BF3 and further treatment with lithium aluminium hydride afforded the corresponding complex aziridine-borane with total selectivity, and no complex of dibenzylamino-borane was detected on the crude reactions. The aziridine-borane complex was isolated, and its structure was established by single-crystal X-ray diffraction analysis: Concellón, J. M, Suárez, J. R, García-Granda, S, Díaz, M. R. Angew. Chem, Int. Ed. 2004, 43, 4333-4336
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3 and further treatment with lithium aluminium hydride afforded the corresponding complex aziridine-borane with total selectivity, and no complex of dibenzylamino-borane was detected on the crude reactions. The aziridine-borane complex was isolated, and its structure was established by single-crystal X-ray diffraction analysis: Concellón, J. M.; Suárez, J. R.; García-Granda, S.; Díaz, M. R. Angew. Chem., Int. Ed. 2004, 43, 4333-4336.
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The same participation of the dibenzylamino group in ring-opening of amino epoxides by ketones was previously proposed: (a) Concellón, J. M, Suárez, J. R, García-Granda, S, Díaz, M. R. Org. Lett. 2005, 7, 247-250
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The same participation of the dibenzylamino group in ring-opening of amino epoxides by ketones was previously proposed: (a) Concellón, J. M.; Suárez, J. R.; García-Granda, S.; Díaz, M. R. Org. Lett. 2005, 7, 247-250.
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