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This research aims to develop a chiral catalytic system for promoting the enantioselective rearrangement of flavone derivatives.

February 28, 2026Organic Letters0 citations

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Chiral N , N ′-Dioxide/Magnesium(II)-Catalyzed Enantioselective 3,3-Sigmatropic Rearrangement of 3-Propargyloxyflavones

DLDeyang LiuSichuan University CCCuihua ChuSichuan University YLYi LiSichuan University

Key Points

This research aims to develop a chiral catalytic system for promoting the enantioselective rearrangement of flavone derivatives.
Developed a chiral N,N′-dioxide/Mg(II) catalytic system.
Investigated the mechanism of the reaction, focusing on C–H···π interactions.
Evaluated the yields and enantiomeric excess (ee) of generated products.
Obtained diverse allene-containing 3-propargyloxyflavone derivatives in moderate to good yields.
Achieved excellent ee values, indicating high enantioselectivity.
Identified water as an accelerator for the transformation.

Abstract

A chiral N,N′-dioxide/Mg(II) catalytic system was developed for the efficient promotion of the enantioselective 3,3-sigmatropic rearrangement of 3-propargyloxyflavones. Diverse allene-containing 3-propargyloxyflavone derivatives were thus obtained in moderate to good yields and excellent ee values. Mechanism investigations revealed that water serves as an accelerator for this transformation, while the C–H···π interaction between the catalyst and the chromone substrates constitutes a rational explanation for chiral recognition.

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Chiral N , N ′-Dioxide/Magnesium(II)-Catalyzed Enantioselective 3,3-Sigmatropic Rearrangement of 3-Propargyloxyflavones

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