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Volumn 65, Issue 42, 2009, Pages 8745-8755

Terminal oxazolinyloxiranes: synthesis, reaction with amines and regioselective β-lithiation

Author keywords

[No Author keywords available]

Indexed keywords

ALKYL GROUP; AMINE; BENZOTRIAZOLE DERIVATIVE; ELECTROPHILE; ETHYLENE OXIDE DERIVATIVE; METHANOL; NUCLEOPHILE; OXAZOLINE DERIVATIVE;

EID: 69849086150     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2009.08.040     Document Type: Article
Times cited : (9)

References (38)
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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:
    • 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
    • (2008) J. Org. Chem. , vol.73 , pp. 9552-9564
    • Capriati, V.1    Florio, S.2    Luisi, R.3    Perna, F.M.4    Spina, A.5
  • 11
    • 69849104608 scopus 로고    scopus 로고
    • Patent, Jpn. Kokai Tokyo Koho, JP 83-47333, 1983
    • Patent, Jpn. Kokai Tokyo Koho, JP 83-47333, 1983.
  • 18
    • 69849108710 scopus 로고    scopus 로고
    • note
    • 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.
  • 20
    • 69849103312 scopus 로고    scopus 로고
    • note
    • 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.
  • 25
    • 9444226868 scopus 로고    scopus 로고
    • For a leading review on β- and γ-amino acids, see:
    • 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
    • (2004) Chem. Biodivers. , vol.1 , pp. 1111-1239
    • Seebach, D.1    Beck, A.K.2    Bierbaum, D.3
  • 29
    • 69849085571 scopus 로고    scopus 로고
    • For leading references on Li/OR carbenoids, see:
    • For leading references on Li/OR carbenoids, see:
  • 32
    • 69849085396 scopus 로고    scopus 로고
    • note
    • 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).
  • 33
    • 0000914237 scopus 로고    scopus 로고
    • For a related work on the in situ silylation of highly reactive terminal oxiranyllithiums, see:
    • 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
    • (2001) Org. Lett. , vol.3 , pp. 461-463
    • Hodgson, D.M.1    Norsikian, S.L.M.2
  • 34
    • 34548192017 scopus 로고    scopus 로고
    • For another example of oxazolinyl-promoted-β-lithiation, see:
    • 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
    • (2007) Org. Lett. , vol.9 , pp. 3295-3298
    • Luisi, R.1    Capriati, V.2    Di Cunto, P.3    Florio, S.4    Mansueto, R.5
  • 36
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    • *)-16) as already reported for similar compounds, see:
    • *)-16) as already reported for similar compounds, see:


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.