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58049204541
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The configurational stability of α-lithiated oxazolinyloxiranes has been recently investigated by means of a multinuclear magnetic resonance study, supported by an in situ IR spectroscopy:
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The configurational stability of α-lithiated oxazolinyloxiranes has been recently investigated by means of a multinuclear magnetic resonance study, supported by an in situ IR spectroscopy:. Capriati V., Florio S., Luisi R., Perna F.M., and Spina A. J. Org. Chem. 73 (2008) 9552-9564
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Patent, Jpn. Kokai Tokyo Koho, JP 83-47333, 1983.
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2OH, see:. Katritzky A.R., Manju K., Singh S.K., and Meher N.K. Tetrahedron 61 (2005) 2555-2581 and references therein
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69849108710
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note
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It is worth noting that terminal oxazolinyloxirane 6c could not be obtained from the corresponding 2-acyl-2-oxazoline because of its instability; indeed, it undergoes a fast rearrangement to the corresponding oxazinone.
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20
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69849103312
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note
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CCDC 720194 contains the supplementary crystallographic data for compound (2R,4′S)-10. These data can be obtained free of charge from The Cambridge Crystallographic Data Centre via www.ccdc.cam.ac.uk. The absolute configuration to the remaining stereoisomers was assigned comparing their optical rotation values and taking into account that of oxazolinyloxirane (2R,4′S)-10.
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0023201816
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9444226868
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For a leading review on β- and γ-amino acids, see:
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For a leading review on β- and γ-amino acids, see:. Seebach D., Beck A.K., and Bierbaum D. Chem. Biodivers. 1 (2004) 1111-1239
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For leading references on Li/OR carbenoids, see:
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69849085396
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note
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H-H splitting is 15.3 Hz. The magnitude of the latter gives evidence for a trans arrangement of the vinylic hydrogens (see Supplementary data).
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33
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0000914237
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For a related work on the in situ silylation of highly reactive terminal oxiranyllithiums, see:
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For a related work on the in situ silylation of highly reactive terminal oxiranyllithiums, see:. Hodgson D.M., and Norsikian S.L.M. Org. Lett. 3 (2001) 461-463
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34548192017
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For another example of oxazolinyl-promoted-β-lithiation, see:
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For another example of oxazolinyl-promoted-β-lithiation, see:. Luisi R., Capriati V., Di Cunto P., Florio S., and Mansueto R. Org. Lett. 9 (2007) 3295-3298
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69849100614
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*)-16) as already reported for similar compounds, see:
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*)-16) as already reported for similar compounds, see:
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37
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