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Volumn 66, Issue 23, 2010, Pages 4167-4194

Alkylation and aldol reactions of acyl derivatives of N-1-(1′-naphthyl)ethyl-O-tert-butylhydroxylamine: asymmetric synthesis of α-alkoxy-, α-substituted-β-alkoxy- and α,β-dialkoxyaldehydes

Author keywords

Aldol reaction; Diastereoselective alkylation; Glycolate enolate; Weinreb amide

Indexed keywords

ALDEHYDE DERIVATIVE; CROWN COMPOUND; GLYCOLIC ACID DERIVATIVE; HALIDE; HYDROXYLAMINE; POTASSIUM DERIVATIVE;

EID: 77953121509     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2010.03.105     Document Type: Article
Times cited : (14)

References (68)
  • 1
    • 77953119584 scopus 로고    scopus 로고
    • For instance, see
    • For instance, see:
  • 7
    • 33748237133 scopus 로고
    • Masamune has also reported a benzopyranoisoxazolidine auxiliary which is capable of acting as a chiral Weinreb amide equivalent; see:
    • Masamune has also reported a benzopyranoisoxazolidine auxiliary which is capable of acting as a chiral Weinreb amide equivalent; see:. Abiko A., Moriya O., Filla S.A., and Masamune S. Angew. Chem., Int. Ed. Engl. 34 (1995) 793
    • (1995) Angew. Chem., Int. Ed. Engl. , vol.34 , pp. 793
    • Abiko, A.1    Moriya, O.2    Filla, S.A.3    Masamune, S.4
  • 12
    • 0036400051 scopus 로고    scopus 로고
    • For selected recent applications of enantiomerically pure 4-alkyl-5,5-dimethyloxazolidin-2-one (SuperQuat) chiral auxiliaries in synthesis from this laboratory, see:
    • For selected recent applications of enantiomerically pure 4-alkyl-5,5-dimethyloxazolidin-2-one (SuperQuat) chiral auxiliaries in synthesis from this laboratory, see:. Davies S.G., Nicholson R.L., and Smith A.D. Synlett (2002) 1637
    • (2002) Synlett , pp. 1637
    • Davies, S.G.1    Nicholson, R.L.2    Smith, A.D.3
  • 18
    • 77953121415 scopus 로고    scopus 로고
    • note
    • The absence of significant amounts of products resulting from the reaction of radical anion 19 or oxonium species 20 with excess alkoxide points to a fast intramolecular reaction occurring within the solvent cage.
  • 24
    • 77953123090 scopus 로고    scopus 로고
    • note
    • 1H NMR spectroscopic analysis in the presence of (S)-O-acetylmandelic acid as a chiral shift reagent, and comparison with an authentic racemic sample.
  • 46
    • 59949097919 scopus 로고    scopus 로고
    • We have recently reported a variant of the Wadsworth-Emmons olefination using MeMgBr as the base, which is amenable to the olefination of stereochemically labile aldehydes; see:
    • We have recently reported a variant of the Wadsworth-Emmons olefination using MeMgBr as the base, which is amenable to the olefination of stereochemically labile aldehydes; see:. Claridge T.D.W., Davies S.G., Lee J.A., Nicholson R.L., Roberts P.M., Russell A.J., Smith A.D., and Toms S.M. Org. Lett. 10 (2008) 5437
    • (2008) Org. Lett. , vol.10 , pp. 5437
    • Claridge, T.D.W.1    Davies, S.G.2    Lee, J.A.3    Nicholson, R.L.4    Roberts, P.M.5    Russell, A.J.6    Smith, A.D.7    Toms, S.M.8
  • 48
    • 77953120446 scopus 로고    scopus 로고
    • note
    • The enantiomeric excesses of 49 and 50 were determined by Chiral GC analysis.
  • 58
    • 77953119993 scopus 로고    scopus 로고
    • note
    • Efforts to achieve an aldol reaction upon treatment of 6 with dibutylboron triflate, triethylamine and benzaldehyde were unsuccessful.
  • 59
    • 77953123838 scopus 로고    scopus 로고
    • note
    • Reversal of diastereoselectivity in aldol reactions of glycolates relative to propionates has been observed; see, for example, Ref. 1a within.
  • 67
    • 77953120300 scopus 로고    scopus 로고
    • note
    • Use of PhMe as the solvent provided a sharper end-point than THF.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.