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Volumn 60, Issue 35, 2004, Pages 7553-7577

N-α-Benzyloxyacetyl derivatives of (S)-4-benzyl-5,5- dimethyloxazolidin-2-one for the asymmetric synthesis of differentially protected α,β-dihydroxyaldehydes

Author keywords

, Dihydroxyaldehydes; Asymmetric aldol

Indexed keywords

ACETIC ACID DERIVATIVE; ALDEHYDE DERIVATIVE; ALIPHATIC COMPOUND; BENZENE DERIVATIVE; BORON; HYDROXYL GROUP; OXAZOLIDINE DERIVATIVE;

EID: 3843095145     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2004.05.123     Document Type: Article
Times cited : (28)

References (59)
  • 23
    • 0022345720 scopus 로고
    • For an isolated example of the direct reduction of an N-acyl oxazolidinone to the corresponding aldehyde see
    • For an isolated example of the direct reduction of an N-acyl oxazolidinone to the corresponding aldehyde see Meyers A.I., Spohn R.F., Linderman R.J. J. Org. Chem. 50:1985;3633
    • (1985) J. Org. Chem. , vol.50 , pp. 3633
    • Meyers, A.I.1    Spohn, R.F.2    Linderman, R.J.3
  • 32
    • 0032478579 scopus 로고    scopus 로고
    • For representative examples of other glycolate aldol reactions see
    • For representative examples of other glycolate aldol reactions see Roush W.R., Pfeifer L.A., Marron T.G. J. Org. Chem. 63:1998;2064
    • (1998) J. Org. Chem. , vol.63 , pp. 2064
    • Roush, W.R.1    Pfeifer, L.A.2    Marron, T.G.3
  • 42
    • 0000157603 scopus 로고
    • α,β is usually in the range of 2-6 Hz for syn-aldol products, and 7-10 Hz for anti-aldol products. For leading references
    • α,β is usually in the range of 2-6 Hz for syn-aldol products, and 7-10 Hz for anti-aldol products. For leading references Stiles M., Winkler R.W., Chang Y.-L., Traynor L. J. Am. Chem. Soc. 86:1964;3337
    • (1964) J. Am. Chem. Soc. , vol.86 , pp. 3337
    • Stiles, M.1    Winkler, R.W.2    Chang, Y.-L.3    Traynor, L.4
  • 48
    • 0034730017 scopus 로고    scopus 로고
    • Caddick et al. have previously used 9-BBNOTf as a Lewis acid for the promotion of asymmetric aldol reactions using N-acyl-a-aminoimidazolin-2-one derivatives; see. and Ref. 8
    • Caddick et al. have previously used 9-BBNOTf as a Lewis acid for the promotion of asymmetric aldol reactions using N-acyl-a-aminoimidazolin-2-one derivatives; see Caddick S., Parr N.J., Pritchard M.C. Tetrahedron Lett. 41:2000;5963. and Ref. 8
    • (2000) Tetrahedron Lett. , vol.41 , pp. 5963
    • Caddick, S.1    Parr, N.J.2    Pritchard, M.C.3
  • 49
    • 0037009019 scopus 로고    scopus 로고
    • Similar tetrahedral carbinols have been reported by Evans et al. upon reduction of N-acyl pyrroles; see
    • Similar tetrahedral carbinols have been reported by Evans et al. upon reduction of N-acyl pyrroles; see Evans D.A., Borg G., Scheidt K.A. Angew. Chem., Int. Ed. Engl. 41:2002;3188
    • (2002) Angew. Chem., Int. Ed. Engl , vol.41 , pp. 3188
    • Evans, D.A.1    Borg, G.2    Scheidt, K.A.3
  • 50
    • 0347380050 scopus 로고    scopus 로고
    • this observation has led to the use of pyrrole as a protecting group for aldehydes;
    • this observation has led to the use of pyrrole as a protecting group for aldehydes; Dixon D.J., Scott M.S., Luckhurst C.A. Synlett. 2003;2317
    • (2003) Synlett , pp. 2317
    • Dixon, D.J.1    Scott, M.S.2    Luckhurst, C.A.3
  • 52
    • 0000227367 scopus 로고
    • With identical spectroscopic properties as the racemic ester previously prepared by
    • With identical spectroscopic properties as the racemic ester previously prepared by Guanti G., Banfi L., Narisano E., Scolastico C. Tetrahedron. 44:1988;3671
    • (1988) Tetrahedron , vol.44 , pp. 3671
    • Guanti, G.1    Banfi, L.2    Narisano, E.3    Scolastico, C.4
  • 56
    • 3843094511 scopus 로고    scopus 로고
    • In the X-ray crystal of 64, the TBDMS group was best modelled as disordered over two sites in the ratio 0.62:0.38 and only the major conformer is shown. The O-benzyl and 4-benzyl-5,5-dimethyloxazolidin-2-one fragments of the structure also contain some disorder which is reflected in the prolated ADPs for the atoms contained within these fragments
  • 57
    • 3843081389 scopus 로고    scopus 로고
    • note
    • C(1′)H-C(2′)H in all N-1′-hydroxy-2′- benzyloxyoxazolidin-2-ones 25-28 and 60-65 arising from DIBAL reduction of the corresponding O-silyl protected aldol products was of a similar magnitude (J>7.5 Hz but <8.8 Hz where it could be established)
  • 58
    • 3843087985 scopus 로고    scopus 로고
    • note
    • Aldehyde 70 was contaminated with <2% of an unknown compound, which could be neither identified, nor removed upon repeated chromatographic purification


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.