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 degrees 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.
Catalytic intramolecular crossed aldehyde--ketone benzoin reactions: a novel synthesis of functionalized preanthraquinones. Publishing Authors By Initials
Catalytic intramolecular crossed aldehyde--ketone benzoin reactions: a novel synthesis of functionalized preanthraquinones. Journal Published:
PUBLICATION TYPE: Journal Article
Journal: Journal of the American Chemical Society
VOLUME: 125
Page Numbers: 8432-3
Journal Abbreviation: J. Am. Chem. Soc.
ISSN: 0002-7863
DAY: 16
MONTH: Jul
YEAR: 2003
Catalytic intramolecular crossed aldehyde--ketone benzoin reactions: a novel synthesis of functionalized preanthraquinones. Information
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LANGUAGE: eng
NlmUniqueID: 7503056
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Grant and Affiliation Information for Catalytic intramolecular crossed aldehyde--ketone benzoin reactions: a novel synthesis of functionalized preanthraquinones.
AFFILIATION: Department of Chemistry, Tokyo Institute of Technology and CREST, Japan Science and Technology Corporation, O-okayama, Meguro-Ku, Tokyo 152-8551, Japan.
Country: United States
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MEDLINETA: J Am Chem Soc
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