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Volumn 19, Issue 10, 2008, Pages 1274-1284

Probing the parallel resolution of Mosher's acid using a combination of quasi-enantiomeric oxazolidin-2-ones

Author keywords

[No Author keywords available]

Indexed keywords

2 METHOXY 2 PHENYL 2 TRIFLUOROMETHYL ACETIC ACID; 2 METHOXY 2 PHENYL 2 TRIFLUOROMETHYLACETIC ACID; 2 PHENYL 2 METHOXY 2 TRIFLUOROETHANONYL)(2 ((BUTOXYCARBONYL)OXY) 2,2 DIPHENYL 2 PHENYLETHYL)CARBAMATE; 4 PHENYL 3 (2 METHOXY 2 PHENYL 2 TRIFLUOROMETHYLACETYL)OXAZOLIDIN 2 ONE; 4 PHENYL 5,5 DIPHENYL 3 (2 METHOXY 2 PHENYL 2 TRIFLUOROMETHYLACETYL)OXAZOLIDIN 2 ONE; ACETIC ACID; BUTYL 2 METHOXY 2 PHENYL 2 TRIFLUOROMETHYL ACETATE; N (2 HYDROXY 1 PHENYLETHYL) 2 PHENYL 2 METHOXY 2 TRIFLUOROMETHYLACETAMIDE; OXAZOLIDIN 2 ENONE; OXAZOLIDINE DERIVATIVE; PENTAFLUOROPHENYL 1 TRIFLUOROMETHYL 1 METHOXY PHENYLACETATE;

EID: 44449137422     PISSN: 09574166     EISSN: 1362511X     Source Type: Journal    
DOI: 10.1016/j.tetasy.2008.04.032     Document Type: Article
Times cited : (3)

References (65)
  • 24
  • 38
    • 44449110336 scopus 로고    scopus 로고
    • note
    • The (R)- and (S)-enantiomer of active ester 10 can be synthesised in 92% and 88%, respectively.
  • 39
    • 44449148570 scopus 로고    scopus 로고
    • note
    • The data relating to the single crystal X-ray structures of (R)-10 has been deposited at the Cambridge Crystallographic Database {CCDC reference number 683188}.
  • 40
    • 44449127854 scopus 로고    scopus 로고
    • note
    • The absolute configurations of each diastereoisomer were assigned by stereospecific synthesis; see Section 4 for details.
  • 42
    • 44449121586 scopus 로고    scopus 로고
    • note
    • The configurational assignment was determined through stereospecific synthesis.
  • 44
    • 44449099423 scopus 로고    scopus 로고
    • note
    • An equimolar amount of (R)-4-Li and rac-13 gave the corresponding adduct (S,R)-syn-14 in 48% yield with 60% de (reported in Yohannes, Y. PhD Thesis, University of London, 2004).
  • 45
    • 44449171720 scopus 로고    scopus 로고
    • note
    • 1H NMR spectroscopy.
  • 53
    • 44449140725 scopus 로고    scopus 로고
    • note
    • The low recoverability of the oxazolidinone (S)-9 was due to its insoluble nature.
  • 57
    • 3843095145 scopus 로고    scopus 로고
    • For a comprehensive account of endo-cleavage of 4-alkyl substituted-5,5-dimethyl-oxazolidin-2-ones (known as SuperQuats) see:
    • For a comprehensive account of endo-cleavage of 4-alkyl substituted-5,5-dimethyl-oxazolidin-2-ones (known as SuperQuats) see:. Davies S.G., Hunter I.A., Nicholson R.L., Roberts P.M., Savory E.D., and Smith A.D. Tetrahedron: Asymmetry 60 (2004) 7553-7577
    • (2004) Tetrahedron: Asymmetry , vol.60 , pp. 7553-7577
    • Davies, S.G.1    Hunter, I.A.2    Nicholson, R.L.3    Roberts, P.M.4    Savory, E.D.5    Smith, A.D.6
  • 59
    • 44449106829 scopus 로고    scopus 로고
    • note
    • 2 prior to use.
  • 60
    • 44449105300 scopus 로고    scopus 로고
    • note
    • 1H NMR spectroscopy.
  • 62
    • 44449117726 scopus 로고    scopus 로고
    • note
    • The enantiomeric excess was determined by DCC coupling with either (R)- or (S)-1-phenylethanol.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.