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Synfacts 2006(9): 0890-0890  
DOI: 10.1055/s-2006-942065
Synthesis of Heterocycles
© Georg Thieme Verlag Stuttgart · New York

Enantioselective Cu-Catalyzed Hetero-Diels-Alder Synthesis of δ-Lactones

Contributor(s): Victor Snieckus, Bärbel Wittel
L. Lin, Q. Fan, B. Qin, X. Feng*
Sichuan University, Chengdu, P. R. of China
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Publication History

Publication Date:
23 August 2006 (online)

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Significance

Two new chiral copper(II) Schiff base complexes have been shown to catalyze the hetero-Diels-Alder reaction of Brassard dienes with a variety of aldehydes to give 5-methyl-α,β-unsaturated δ-lactones in moderate yields but with excellent diastereo- and enantioselectivity. A series of aromatic and heteroaromatic aldehydes bearing electron-withdrawing and -donating groups were employed. Other chiral tridentate Schiff base ligands, Lewis acids and conditions were tested with less effective results.