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Article Abstract
A microwave-assisted cascade conjugate addition-intramolecular cinnamoyl transfer ("cut and sew") strategy involving 2-hydroxyphenyl--quinone methides (HPQMs) and curcumins, yielding cinnamoyl cinnamates bearing a diarylalkyl moiety in excellent yields and with broad substrate versatility, is reported. Mechanistic studies revealed a cascade Michael-hemiketalization-retro-Claisen reaction resulting in the C-C(CO) bond cleavage of curcumin. Furthermore, the cinnamoyl transfer products are amenable for a variety of synthetic transformations, highlighting their significance and synthetic utility.
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