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2OBn, see: (a) Amoroso, R.; Cardillo, G.; Sabatino, P.; Tomasini, C.; Trerè, A. J. Org. Chem. 1993, 58, 5615-5619. For cyclization to trans aziridine, see:
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16
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0042751439
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note
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3).
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17
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0043252551
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note
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It is generally assumed that the ring expansion of N-acylaziridine occurs via a carbocationic-like TS (ref 3a) or a carbocationic intermediate (ref 3b) and is favored by the presence of Lewis acids. (equation presented) Our semiempirical calculations suggest that the presence of the imidazolidin-2-one substituent could be responsible for the accelerated expansion rate. Indeed, the reactant adopts a preferential conformation in which the endocyclic carbonylic oxygen points toward the aziridine C3′, thus stabilizing the incipient positive charge. This model is in accord with our previous experimental observations that aziridine 2-ester ring expansion is much slower than that of aziridine 2-imide.
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20
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0042250033
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note
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3).
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21
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0030039884
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For an alternative method for the direct introduction of hydroxyamino acids starting from heterocyclic compounds, see: (a) Palomo, C.; Aizpurua, J. M.; Ganboa, I.; Odriozola, B.; Maneiro, E.; Miranda, J. I.; Urchegui, R. Chem. Commun. 1996, 161-162.
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Palomo, C.1
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Ganboa, I.3
Odriozola, B.4
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Miranda, J.I.6
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(b) Palomo, C.; Cabrè, F.; Ontoria, J. M. Tetrahedron Lett. 1992, 33, 4819-4822.
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Palomo, C.1
Cabrè, F.2
Ontoria, J.M.3
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