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Volumn 33, Issue 20, 1994, Pages 2098-2100

[2,3] Sigmatropic Wittig Rearrangement of Chiral Allyloxyacetaldehyde Hydrazones in the Diastereo‐ and Enantioselective Synthesis of Protected, γ,δ‐Unsaturated α‐Hydroxyaldehydes and Cyanohydrins

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EID: 33748232901     PISSN: 05700833     EISSN: 15213773     Source Type: Journal    
DOI: 10.1002/anie.199420981     Document Type: Article
Times cited : (32)

References (86)
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    • Brückner, R.1
  • 31
    • 84984348909 scopus 로고
    • Asymmetric Induction in the Wittig-Still Rearrangement of Ethers Containing an Allylic Stereocenter – Diastereocontrol by Allylic Oxygen
    • (1990) Chemische Berichte , vol.123 , pp. 153
    • Priepke, H.1    Brückner, R.2
  • 61
    • 0000710861 scopus 로고
    • Synthese und Reaktionen optisch aktiver Cyanhydrine
    • (c) For enzymatic reactions of optically active cyanohydrins see
    • (1994) Angewandte Chemie , vol.106 , pp. 1609
    • Effenberger, F.1
  • 64
    • 84989510851 scopus 로고    scopus 로고
    • (a) Synthesis of the hydrazones (S)‐1: The aldehydes, obtained by reaction of the allyl alcohols with ethyl bromoacetate, bromoacetaldehyde diethyl acetal, or 3‐chloro‐l,2‐propanediol followed by reduction with DIBAH, acidic cleavage of the acetal or sodium periodate cleavage of the diol, were transformed to hydrazone (S)‐1 with SAEP
  • 66
    • 84989511809 scopus 로고    scopus 로고
    • By the rearrangement of the sterically less demanding (S)‐l‐amino‐2‐methoxymethylpyrrolidine (SAMP) hydrazone, analogous to (S)‐la, significantly lower asymmetric induction was achieved (93% syn, 57% de).
  • 69
    • 84989588794 scopus 로고
    • For oxidative MMPP cleavage of ketohydrazones see, Synlett
    • (1990) , pp. 725
    • Enders, D.1    Plant, A.2
  • 70
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    • The cis selectivity of the iodocyclization amounted to 75%.
  • 86
    • 84989533180 scopus 로고    scopus 로고
    • All new compounds gave correct elemental analysis and consistent spectroscopic data (IR, NMR, MS).


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.