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Volumn 63, Issue 48, 2007, Pages 12047-12057

Diastereoselective intramolecular acyl transfer of 5-(α-methylbenzyl)amino-1,3-dioxan-2-one to 4-hydroxymethyl-2-oxazolidinones

Author keywords

Acyl transfer; Asymmetric desymmetrization; Oxazolidinone; Serinol

Indexed keywords

4 HYDROXYMETHYL 3ALPHA METHYLBENZYL 2 OXAZOLIDINONE; 5 (ALPHA METHYLBENZYL)AMINO 1,3 DIOXAN 2 ONE; DIMETHYL SULFOXIDE; DIOXANE DERIVATIVE; OXAZOLIDINONE DERIVATIVE; UNCLASSIFIED DRUG;

EID: 35348857425     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2007.09.004     Document Type: Article
Times cited : (2)

References (33)
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    • 35348891225 scopus 로고    scopus 로고
    • In general, a treatment of 4-(1-hydroxy)alkyl-2-oxazolidinones E with bases led to an intramolecular acyl transfer of the oxazolidinone rings to give corresponding isomers of 2-oxazolidinones F:. {A figure is presented}
  • 9
    • 0001589756 scopus 로고
    • {A figure is presented}
    • Roush W.R., and Adam M.A. J. Org. Chem. 50 (1985) 3752-3760. {A figure is presented}
    • (1985) J. Org. Chem. , vol.50 , pp. 3752-3760
    • Roush, W.R.1    Adam, M.A.2
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    • {A figure is presented}
    • Wee A.G.H., and McLeod D.D. J. Org. Chem. 68 (2003) 6268-6273. {A figure is presented}
    • (2003) J. Org. Chem. , vol.68 , pp. 6268-6273
    • Wee, A.G.H.1    McLeod, D.D.2
  • 21
    • 35348830151 scopus 로고    scopus 로고
    • note
    • 1H NMR integration.
  • 22
    • 22144477561 scopus 로고    scopus 로고
    • Synthesis of 3-benzyl-5-hydroxymethyl-2-oxazolidinone from halomethyloxiranes via 3-benzyl-5-hydroxy-3,4,5,6-tetrahydro-1,3-oxazin-2-one and then a 6-aza-2,7-dioxabicyclo[2.2.1]heptane derivative as proposal intermediates has been reported:
    • Synthesis of 3-benzyl-5-hydroxymethyl-2-oxazolidinone from halomethyloxiranes via 3-benzyl-5-hydroxy-3,4,5,6-tetrahydro-1,3-oxazin-2-one and then a 6-aza-2,7-dioxabicyclo[2.2.1]heptane derivative as proposal intermediates has been reported:. Osa Y., Hikima Y., Sato Y., Takino K., Ida Y., Hirono S., and Nagase H. J. Org. Chem. 70 (2005) 5737-5740
    • (2005) J. Org. Chem. , vol.70 , pp. 5737-5740
    • Osa, Y.1    Hikima, Y.2    Sato, Y.3    Takino, K.4    Ida, Y.5    Hirono, S.6    Nagase, H.7
  • 23
    • 35348891805 scopus 로고    scopus 로고
    • note
    • 3/MeOH, 95:5) gave cyclic carbonate 2 (21%) and a mixture of oxazolidinones (4S)-3 and (4R)-3 (92:8, 33%). Presumably, slow purification using silica gel column chromatography increased the yield of the oxazolidinones.
  • 26
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    • A review of fluoride ion as a base in organic synthesis:
    • A review of fluoride ion as a base in organic synthesis:. Clark J.H. Chem. Rev. 80 (1980) 429-452
    • (1980) Chem. Rev. , vol.80 , pp. 429-452
    • Clark, J.H.1
  • 27
    • 35348898203 scopus 로고    scopus 로고
    • note
    • 3 was kept for 2.5 days at room temperature; however, no acyl transfer proceeded. Identical results were also observed using (4R)-3.
  • 28
    • 35348892933 scopus 로고    scopus 로고
    • note
    • 3OD.
  • 31


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.