Synlett 2024; 35(18): 2123-2127
DOI: 10.1055/a-2288-3074
letter

Regiocontrolled Ruthenium-Catalyzed Isomerization of Propargyl Alcohols

Steffen Skowaisa
,
Edgar Haak

This work was supported by the German Research Foundation (Deutsche Forschungsgemeinschaft, DFG; No. 265182801).


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Abstract

A diaminocyclopentadienone ruthenium complex allows control of regioselectivity in the ruthenium-catalyzed isomerization of propargyl alcohols through the choice of additive. Thereby, both products of the Meyer–Schuster rearrangement and redox isomerization products are selectively accessible. In the presence of hydroxylamine-O-sulfonic acid, unsaturated nitriles are formed instead. The ruthenium catalyst is readily available and stable to moisture, air, and acidic conditions.

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Publikationsverlauf

Eingereicht: 07. Februar 2024

Angenommen nach Revision: 14. März 2024

Accepted Manuscript online:
14. März 2024

Artikel online veröffentlicht:
02. April 2024

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