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Volumn 2, Issue 2, 1997, Pages 81-98

Exerting face-stereoselective shielding: Design of an enantiomeric pair of camphene-based oxazolidin-2-ones for use as recyclable chiral auxiliaries in asymmetric synthesis

Author keywords

Asymmetric synthesis; Chiral auxiliaries; Oxazolidin 2 ones

Indexed keywords

2 OXAZOLIDINONE DERIVATIVE; DIHYDROPROTOLICHESTERINIC ACID; FATTY ACID DERIVATIVE; TERPENE DERIVATIVE; UNCLASSIFIED DRUG;

EID: 0030841909     PISSN: 10242430     EISSN: None     Source Type: Journal    
DOI: None     Document Type: Review
Times cited : (6)

References (49)
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    • We have prepared the exo-variant of 1 from exo-borneol [obtained by L-Selectride reduction of (1R)-camphor] using our nitreno-mediated route to construct the oxazolidin-2-one ring (G.B. patent application No. 901268.0, filing date 7th July 1990); see also Bonner, M. P. and Thornton, E. R. (1991). J. Am. Chem. Soc., 113, 1299 for an alternative synthesis from (1R)-(-)-camphorquinone by conversion into the corresponding exo,exo-aminoalcohol followed by cyclocarbamation.
    • (1991) J. Am. Chem. Soc. , vol.113 , pp. 1299
    • Bonner, M.P.1    Thornton, E.R.2
  • 18
    • 0028901621 scopus 로고
    • Davies, S. G. and Sanganee, H. J. (1993). Tetrahedron Asymmetry, 6, 671 and references therein of the need of steric shielding for clean removal and recycling of oxazolidin-2-one auxiliaries.
    • (1993) Tetrahedron Asymmetry , vol.6 , pp. 671
    • Davies, S.G.1    Sanganee, H.J.2
  • 25
    • 0343205965 scopus 로고    scopus 로고
    • Banks, M. R., Cadogan, J. I. G., Gosney, I., Hodgson, P. K. G. and Thorburn, P. (1996). Acros Chimica Acta, 2, 14, [Chiracamphox, is commercially available in both enantiomeric forms from Acros Chimica N.V. Janssen Pharmaceuticalaan 3,2440, Geel, Belgium, Cat. Nos. 29643-5000 and 30065-5000 for (-)- and (+)-forms, respectively.
    • (1996) Acros Chimica Acta , vol.2 , pp. 14
    • Banks, M.R.1    Cadogan, J.I.G.2    Gosney, I.3    Hodgson, P.K.G.4    Thorburn, P.5
  • 26
    • 0027462436 scopus 로고
    • 2 to toluene. Since our original observation [2] we have also discovered that the diastereoselectivity can be improved by changing the order of addition of Lewis Acid promoter to last.
    • (1993) Tetrahedron Asymm. , vol.4 , pp. 629
    • Tanaka, K.1    Uno, H.2    Osuga, H.3    Suzuki, H.4
  • 32
    • 0000584420 scopus 로고
    • ed. J. D. Morrison, Academic Press, New York
    • Heathcock, C. R. (1984). In Asymmetric Synthesis, ed. J. D. Morrison, Academic Press, New York, 3, 154;
    • (1984) Asymmetric Synthesis , vol.3 , pp. 154
    • Heathcock, C.R.1
  • 39
    • 84889557481 scopus 로고
    • Chem. Abstr., 1965, 73, 1996b;
    • (1965) Chem. Abstr. , vol.73
  • 42
    • 84889533335 scopus 로고
    • Chem. Abstr., 1980, 100, 179463f;
    • (1980) Chem. Abstr. , vol.100


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.