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Stereocontrolled synthesis of 3-alkylindolines from (Z)-2-hydroxyindolenines

Stereokontrollierte Synthese von 3-Alkylindolinen aus (Z)-2-Hydroxyindoleninen

  • Organische Chemie Und Biochemie
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Summary

A convenient process for the synthesis of 3-alkylindolines2 and their transformation intocis-fused tricyclic γ-lactones3 from allylic alcohols1, mediated by aGrignard reagent, is described. This process proceeds with high stereocontrol at the two newly formed contiguous stereogenic centres. By oxidation with chromium oxide, 2-oxindole derivatives4 are obtained from 3-alkylindolines2.

Zusammenfassung

Eine einfache Methode zur Herstellung der 3-Alkylindoline2 und deren Umsetzung zu dencis-kondensierten tricyclischen γ-Lactonen3 aus den Allylalkoholen1 mittels einerGrignard-Verbindung wird beschrieben. Die Reaktion verläuft unter hoher Stereoselektivität bezüglich der zwei neu gebildeten Asymmetriezentren. Durch Oxidation mit Chromtrioxid erhält man aus den 3-Alkylindolinen2 die 2-Oxindolderivate4.

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Authors and Affiliations

  1. Departamento de Química del Centro de Investigación y der Estudios Avancados, Instituto Politécnico Nacional, 07000, México, D.F., México

    M. S. Morales-Ríos, C. García-Martínez, M. A. Bucio & P. Joseph-Nathan

Authors
  1. M. S. Morales-Ríos
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  2. C. García-Martínez
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  3. M. A. Bucio
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  4. P. Joseph-Nathan
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Morales-Ríos, M.S., García-Martínez, C., Bucio, M.A. et al. Stereocontrolled synthesis of 3-alkylindolines from (Z)-2-hydroxyindolenines. Monatsh Chem 127, 691–699 (1996). https://doi.org/10.1007/BF00817260

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  • DOI: https://doi.org/10.1007/BF00817260

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