Substrate-Controlled Regioselective Cascade Reactions of Deconjugated Butenolides and Cinnamaldehydes: Access to
Juan-Ru Tian1, Hang Qin1, Lanbo Liu1
1College of Pharmaceutical Sciences, Hebei University, Baoding 071002, China.
Abstract:
Two different cascade pathways to access spirobutenolides were achieved based on the substrate-controlled regioselectivity of deconjugated butenolides. A new class of functional deconjugated butenolides was designed and exhibited superior γ-regioselectivity in the vinylogous Michael/Michael cascade reactions with cinnamaldehydes. The aryl-substituted deconjugated butenolides and cinnamaldehydes underwent a Michael/Michael/aldol/dehydration cascade process induced by double α-regioselectivities. Both conjugated and deconjugated spirobutenolides could be obtained in good yields with excellent enantioselectivities.
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