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Synthesis of Cyclopentenones with C4-Quaternary Stereocenters via Stereospecific [3,3]-Sigmatropic Rearrangement and Applications in Total Synthesis of Sesquiterpenoids

Weiping Zhou and Arnaud Voituriez*

*Université Paris-Saclay, CNRS, Institut de Chimie des Substances Naturelles, UPR 2301, 91198 Gif-sur-Yvette, France, Email:

W. Zhou, A. Voituriez, J. Am. Chem. Soc., 2021, 143, 17348-17353.

DOI: 10.1021/jacs.1c07966

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A cationic gold(I)-catalyzed stereospecific [3,3]-sigmatropic rearrangement provides cyclopentenones with a C4-quaternary stereocenter starting from simple chiral vinyl sulfoxides and a propargyl silane.

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proposed mechanism and transition state

Key Words

cyclopentenones, aldol condensation

ID: J48-Y2021