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DOI: 10.1055/s-0036-1588340
Structure-Dependent Nickel-Catalysed Transposition of N-Allylamides to E- or Z-Enamides
Publication History
Received: 10 October 2016
Accepted: 13 October 2016
Publication Date:
14 November 2016 (online)
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Dedicated to Prof. Dieter Enders on the occasion of his 70th birthday
Abstract
The nickel-catalysed transposition of a carbon–carbon double bond of N-allyl and N-homoallyl amides is described. While the transposition of acyclic amides gave very high Z-selectivity of the enamides, corresponding cyclic N-allyl amides led exclusively to the E-configured products. Thereby, we realised a stereodivergent approach to enamides that is dependent on the structure of the amide substituents. When homoallylic substrates are used, a temperature-controlled single transposition to a Z-allylic amide derivative at low temperature or a double transposition to an E-enamide at elevated temperature could be achieved.
Supporting Information
- Supporting information for this article is available online at http://dx.doi.org/10.1055/s-0036-1588340.
- Supporting Information
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For ruthenium and rhodium-catalysed transpositions of N-allyl amides and selected follow-up reactions, see:
For selected iron-catalysed transpositions of N-allyl amides, see:
For selected nickel-catalysed transpositions of N-allyl amides, see: