Issue 5, 2022

On the mechanism of the dyotropic expansion of hydrindanes into decalins

Abstract

A combined computational/experimental approach has revealed key mechanistic aspects in a recently reported dyotropic expansion of hydrindanes into decalins. While computer simulations had already anticipated the need for acid catalysis for making this reaction feasible under the mild conditions used in the laboratory, this work places the dyotropic step not into the reaction flask but at a later step, during the work up instead. With this information in hand the reaction has been optimized by exploring the performance of different activating agents and shown to be versatile, particularly in steroid related chemistry due to the two scaffolds that this reaction connects. Finally, the scope of the reaction has been significantly broadened by showing that this protocol can also operate in the absence of the fused six-member ring.

Graphical abstract: On the mechanism of the dyotropic expansion of hydrindanes into decalins

Supplementary files

Article information

Article type
Paper
Submitted
02 nov. 2021
Accepted
07 janv. 2022
First published
07 janv. 2022

Org. Biomol. Chem., 2022,20, 1073-1079

On the mechanism of the dyotropic expansion of hydrindanes into decalins

H. Santalla, O. Nieto Faza, G. Gómez, Y. Fall and C. S. López, Org. Biomol. Chem., 2022, 20, 1073 DOI: 10.1039/D1OB02150H

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