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: Arnaud.voituriez
cnrs.fr
W. Zhou, A. Voituriez, J. Am. Chem. Soc., 2021, 143, 17348-17353.
DOI: 10.1021/jacs.1c07966
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Abstract
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
