Issue 21, 2022

Palladium-catalyzed enantioselective domino ring-opening/Hiyama coupling of cyclobutanones: development and application to the synthesis of (+)-herbertene-1,14-diol

Abstract

We report a palladium-catalyzed enantioselective domino ring-opening/Hiyama coupling of cyclobutanones with alkenyl-[2-(hydroxymethyl)phenyl]dimethylsilanes, providing 1-indanones bearing a versatile alkenyl group and an all-carbon quaternary center. Our methodology was utilized as the key step in the asymmetric total synthesis of (+)-herbertene-1,14-diol.

Graphical abstract: Palladium-catalyzed enantioselective domino ring-opening/Hiyama coupling of cyclobutanones: development and application to the synthesis of (+)-herbertene-1,14-diol

Supplementary files

Article information

Article type
Research Article
Submitted
02 aug 2022
Accepted
13 sep 2022
First published
16 sep 2022

Org. Chem. Front., 2022,9, 5798-5801

Palladium-catalyzed enantioselective domino ring-opening/Hiyama coupling of cyclobutanones: development and application to the synthesis of (+)-herbertene-1,14-diol

W. Gan, J. Cao and L. Xu, Org. Chem. Front., 2022, 9, 5798 DOI: 10.1039/D2QO01239A

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