Primary‐Amine‐Catalyzed Enantioselective Intramolecular Aldolizations

Zhou, Jian; Wakchaure, Vijay; Kraft, Philip; List, Benjamin

doi:10.1002/anie.200802497

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Primary‐Amine‐Catalyzed Enantioselective Intramolecular Aldolizations

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Zhou, Jian
Research Department Schüth, Max-Planck-Institut für Kohlenforschung, Max Planck Society;

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Wakchaure, Vijay
Research Department List, Max-Planck-Institut für Kohlenforschung, Max Planck Society;

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List, Benjamin
Research Department List, Max-Planck-Institut für Kohlenforschung, Max Planck Society;

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引用

Zhou, J., Wakchaure, V., Kraft, P., & List, B. (2008). Primary‐Amine‐Catalyzed Enantioselective Intramolecular Aldolizations. Angewandte Chemie International Edition, 47(40), 7656-7658. doi:10.1002/anie.200802497.

引用: https://hdl.handle.net/11858/00-001M-0000-000F-90D9-0

要旨

Aldol cyclodehydration of 4‐substituted‐2,6‐heptanediones leads to enantiomerically enriched 5‐substituted‐3‐methyl‐2‐cyclohexene‐1‐ones, which serve as perfume ingredients and valuable synthetic building blocks. Primary amines derived from cinchona alkaloids in combination with acetic acid are efficient catalysts for this transformation, which deliver both enantiomers of the celery ketone.