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Volumn 66, Issue 13, 2010, Pages 2363-2372

Aspects of stereocontrol in the L-Selectride reduction of 4-acyl-1,3-dioxolane derivatives

Author keywords

Diastereoselective; Ketones; Lactols; Polyols

Indexed keywords

1,3 DIOXOLANE DERIVATIVE; KETONE DERIVATIVE; REDUCING AGENT; SELECTRIDE; UNCLASSIFIED DRUG; ZINC CHLORIDE;

EID: 77349084149     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2010.01.107     Document Type: Article
Times cited : (16)

References (30)
  • 2
    • 77349097606 scopus 로고    scopus 로고
    • For example
    • For example:
  • 12
    • 77349109530 scopus 로고    scopus 로고
    • note
    • 1H NMR analysis of the crude reduction product mixtures was possible for the ketone substrates but not for the lactol substrates. In the latter, the free alcohols were released from boron-containing residues only during column chromatography and, for these, ratios are quoted based on yields of isolated products.
  • 13
    • 77349087599 scopus 로고    scopus 로고
    • For example
    • For example:
  • 19
    • 0037416888 scopus 로고    scopus 로고
    • Ref. 8b represents another potential source of stereochemical confusion because the Felkin-Anh explanation presented in Scheme 3 of that paper predicts the opposite outcome (S) to that ('3a,bR') which it is supposed to model
    • Navarre J.-M., Guianvarc'h D., Farese-Di Giorgio A., Condom R., and Benhida R. Tetrahedron Lett. 44 (2003) 2199-2202 Ref. 8b represents another potential source of stereochemical confusion because the Felkin-Anh explanation presented in Scheme 3 of that paper predicts the opposite outcome (S) to that ('3a,bR') which it is supposed to model
    • (2003) Tetrahedron Lett. , vol.44 , pp. 2199-2202
    • Navarre, J.-M.1    Guianvarc'h, D.2    Farese-Di Giorgio, A.3    Condom, R.4    Benhida, R.5
  • 22
    • 77349108397 scopus 로고    scopus 로고
    • note
    • 1H NMR data of the reduced products with those of earlier reduction products. In particular it was noted that the CHAr resonance usually appeared as a slightly broadened singlet (i.e., unresolved multiplet) in the syn- isomers and as a clear doublet (J 8.5-9.5 Hz) for the anti-isomers.
  • 23
    • 77349096913 scopus 로고    scopus 로고
    • note
    • 2-free case the unidentified 'complex' was still present and could only be removed (although not isolated) when chromatography was performed on basic alumina.
  • 25
    • 77349093575 scopus 로고    scopus 로고
    • note
    • Commercially available from Aldrich Chemical Company.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.