Primary-Amine-Catalyzed Enantioselective Intramolecular Aldolizations†
Jian Zhou Dr.
Max-Planck-Institut für Kohlenforschung, Kaiser Wilhelm-Platz 1, 45470 Mülheim an der Ruhr (Germany), Fax: (+49) 208-306-2982
Search for more papers by this authorVijay Wakchaure Dr.
Max-Planck-Institut für Kohlenforschung, Kaiser Wilhelm-Platz 1, 45470 Mülheim an der Ruhr (Germany), Fax: (+49) 208-306-2982
Search for more papers by this authorPhilip Kraft Dr.
Givaudan Schweiz AG, 8600 Dübendorf (Switzerland)
Search for more papers by this authorBenjamin List Prof. Dr.
Max-Planck-Institut für Kohlenforschung, Kaiser Wilhelm-Platz 1, 45470 Mülheim an der Ruhr (Germany), Fax: (+49) 208-306-2982
Search for more papers by this authorJian Zhou Dr.
Max-Planck-Institut für Kohlenforschung, Kaiser Wilhelm-Platz 1, 45470 Mülheim an der Ruhr (Germany), Fax: (+49) 208-306-2982
Search for more papers by this authorVijay Wakchaure Dr.
Max-Planck-Institut für Kohlenforschung, Kaiser Wilhelm-Platz 1, 45470 Mülheim an der Ruhr (Germany), Fax: (+49) 208-306-2982
Search for more papers by this authorPhilip Kraft Dr.
Givaudan Schweiz AG, 8600 Dübendorf (Switzerland)
Search for more papers by this authorBenjamin List Prof. Dr.
Max-Planck-Institut für Kohlenforschung, Kaiser Wilhelm-Platz 1, 45470 Mülheim an der Ruhr (Germany), Fax: (+49) 208-306-2982
Search for more papers by this authorThe authors acknowledge generous funding from the Max Planck Society, the DFG (SPP 1179, Organocatalysis), the Fonds der Chemischen Industrie, and Wacker Chemie AG.
Graphical Abstract
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.
Supporting Information
Supporting information for this article is available on the WWW under http://www.wiley-vch.de/contents/jc_2002/2008/z802497_s.pdf or from the author.
Please note: The publisher is not responsible for the content or functionality of any supporting information supplied by the authors. Any queries (other than missing content) should be directed to the corresponding author for the article.
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