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Synlett 2011(20): 2907-2912  
DOI: 10.1055/s-0031-1289892
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© Georg Thieme Verlag Stuttgart ˙ New York

Asymmetric Inverse-Electron-Demand Hetero-Diels-Alder Reaction via Enamine-Metal Lewis Acid Bifunctional Catalysis

Zhenghu Xu*a, Hong Wang*b
a Key Lab of Colloid and Interface Chemistry of Ministry of Education, School of Chemistry and Chemical Engineering, Shandong, University, No. 27 South Shanda Road, Jinan 250100, Shandong Province, P. R. of China
e-Mail: xuzh@sdu.edu.cn;
b Department of Chemistry and Biochemistry, Miami University, 254 Hughes Laboratories, 701 E High Street, Oxford, OH 45056, USA
Fax: +1(513)5295715; e-Mail: wangh3@muohio.edu;
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Publikationsverlauf

Received 18 August 2011
Publikationsdatum:
23. November 2011 (online)

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Abstract

This paper describes the development of an efficient and atom-economic asymmetric inverse-electron-demand hetero-­Diels-Alder reaction of six-membered ketones with β,γ-unsaturated α-keto esters via enamine-metal Lewis acid bifunctional catalysis.

Key words

asymmetric catalysis - bifunctional catalysis - enamines - Lewis acids - ketones - Hetero-Diels-Alder reaction

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11

Other types of catalytic systems combining enamine catalysis with metal catalysis have also been reported recently. In these systems, the enamine catalysis and
the metal catalysis occur in sequence, see refs. 10o-t