Structural Property of Separable Amide Rotamers: Isomerization through the Formation of the Lithium Enolate.

DOI

Bibliographic Information

Other Title
  • "常温でも分離可能なアミド配座異性体の構造特性：

Description

2,4,6-Tri-tert-butyl anilide derivatives are unique compounds which can be isolated rotational isomers based on amide bond at rt. Recently, we succeeded in the highly selective stereodivergent synthesis of E- and Z-rotamers of these anilide derivatives using Pd chemistry. We report here on the novel structural property of 2,4,6-tri-tert-butylanilide. Namely, interconversion between the separable 2,4,6-tri-tert-butylanilide rotamers was found to easily occur at rt through formation of the lithium enolate. Protonation of the anilide enolate gave the anilide rotamer mixture of E-major. On the other hand, reactions of lithium enolate prepared from 2,4,6-tri-tert-butylpropionanilide with alkyl bromides preferentially afforded a Z-rotamer of alkylated products. In particular, n-propylation with the enolate from E-rotamer occurred with almost complete inversion of the rotational isomerism.

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Details 詳細情報について

  • CRID
    1390001205633502464
  • NII Article ID
    130006995605
  • DOI
    10.14895/hannou.37.0.56.0
  • Text Lang
    ja
  • Data Source
    • JaLC
    • CiNii Articles
  • Abstract License Flag
    Disallowed

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