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Catalytic Intramolecular Crossed Aldehyde−Ketone Benzoin Reactions:  A Novel Synthesis of Functionalized Preanthraquinones

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posted on 21.06.2003, 00:00 by Yoshifumi Hachisu, Jeffrey W. Bode, Keisuke Suzuki
Stereochemically and functionally rich polycyclic compounds are obtained by the first crossed aldehyde−ketone benzoin reaction in excellent yield under mild reaction conditions (5−20 mol % thiazolium salt, 10−70 mol % DBU, tBuOH, 40 °C, 30 min). This novel catalytic methodology offers a convenient approach to sophisticated molecular architectures useful for the stereocontrolled construction of polycyclic compounds as well as the fully regiocontrolled synthesis of anthra- and naphthoquinones.

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