Catalytic Intramolecular Crossed Aldehyde−Ketone Benzoin Reactions: A Novel Synthesis of Functionalized Preanthraquinones
- 21 June 2003
- journal article
- research article
- Published by American Chemical Society (ACS) in Journal of the American Chemical Society
- Vol. 125 (28) , 8432-8433
- https://doi.org/10.1021/ja035308f
Abstract
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.Keywords
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