Primary-Amine-Catalyzed Enantioselective Intramolecular Aldolizations

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 effi...

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Bibliographic Details
Published in:	Angewandte Chemie (International ed.) Vol. 47; no. 40; pp. 7656 - 7658
Main Authors:	Zhou, Jian, Wakchaure, Vijay, Kraft, Philip, List, Benjamin
Format:	Journal Article
Language:	English
Published:	Weinheim Wiley-VCH Verlag 22-09-2008 WILEY-VCH Verlag WILEY‐VCH Verlag
Subjects:	aldol reaction asymmetric catalysis bifunctional catalysis enamines organocatalysis
Online Access:	Get full text
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Summary:	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.
Bibliography:	http://dx.doi.org/10.1002/anie.200802497 ark:/67375/WNG-VHKZS6G2-F Wacker Chemie AG ArticleID:ANIE200802497 Fonds der Chemischen Industrie Max Planck Society The authors acknowledge generous funding from the Max Planck Society, the DFG (SPP 1179, Organocatalysis), the Fonds der Chemischen Industrie, and Wacker Chemie AG. DFG - No. SPP 1179 istex:BE73E4386A114ECAA9107FA77B088A7B864B28EC ObjectType-Article-1 SourceType-Scholarly Journals-1 ObjectType-Feature-2 content type line 23
ISSN:	1433-7851 1521-3773
DOI:	10.1002/anie.200802497