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33746906532
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note
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For Sc(III) and Ni(II), excellent endoselectivity (>99:1) with poor enantioselectivity (max 6% ee) was observed. For Cu(II), a high dr (>99: 1) with low ee (23%) and a low dr (3.5:1) with moderate ee (46% and 58%) were observed.
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24
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84944648082
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For the ionic radii of lanthanide cations, see: Shannon, R. D. Acta Crystallogr. 1976, A32, 751-767.
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Ce(IV) triflate was prepared from CAN and dispensed from a glovebox. For the preparation of Ce(IV) triflate, see: Imamoto, T.; Koide, Y.; Hiyama, S. Chem. Lett. 1990, 1445-1446.
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Imamoto, T.1
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33746862394
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note
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The addition of 4 Å MS to the reaction mixture of catalyst 1, 2-acyl imidazole, and (Z)-N-benzylidene(phenyl)methanamine oxide in ethyl acetate (Table 2, entry I) raised the endo:exo diastereoselectivity from 22:1 to >99: 1, the enantioselectivity from 71% ee to 98% ee, and the yield from 86% to 97%.
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32
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note
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This absolute stereoconfiguration was consolidated via Mosher's ester analysis and optical rotation comparison with a known compound. Details are provided in the Supporting Information. The stereochemistry of all the other isoxazolidines was assigned by analogy.
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