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Chiral N,N'-Dioxide/Magnesium(II)-Catalyzed Enantioselective [3,3]-Sigmatropic Rearrangement of
Deyang Liu1, Cuihua Chu1, Yi Li1
1Key Laboratory of Green Chemistry & Technology, Ministry of Education, College of Chemistry, Sichuan University, Chengdu 610064, China.
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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