Reversal of Product Configuration in Michael Additions of Lithium Enolates to E- and Z-1-Nitro-1-propene

Authors

  • Robert Häner Laboratorium für Organische Chemie der Eidgenössischen Technischen Hochschule, ETH-Zentrum, Universitätstrasse 16, CH-8092 Zürich (Switzerland)
  • Thomas Laube Laboratorium für Organische Chemie der Eidgenössischen Technischen Hochschule, ETH-Zentrum, Universitätstrasse 16, CH-8092 Zürich (Switzerland)
  • Dieter Seebach Laboratorium für Organische Chemie der Eidgenössischen Technischen Hochschule, ETH-Zentrum, Universitätstrasse 16, CH-8092 Zürich (Switzerland)

DOI:

https://doi.org/10.2533/chimia.1984.255

Abstract

The lithium enolates of certain aldehydes, ketones and esters are added to E- or Z-nitropropene with stereochemical control by the nitroolefin configuration (products 1-5). The configuration of the major diastereomers of the 2.3-dialkylated 4-nitro-carbonyl derivatives thus obtained in selectivities of 60:40 to 97:3 was assigned by comparison with literature data and by chemical correlation. Cases, in which no reversal of product configuration can be achieved by switching from E- to Z-nitropropene, are also identified.

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Published

1984-08-31

Issue

Vol. 38 No. 7-8 (1984): Forschung/Research

Section

Kurze Mitteilungen

License

Copyright (c) 1984 Robert Häner

Creative Commons License

This work is licensed under a Creative Commons Attribution 4.0 International License.

How to Cite

[1]
R. Häner, T. Laube, D. Seebach, Chimia 1984, 38, 255, DOI: 10.2533/chimia.1984.255.