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Synfacts 2010(10): 1196-1196  
DOI: 10.1055/s-0030-1258678
Organo- and Biocatalysis
© Georg Thieme Verlag Stuttgart ˙ New York

Crotonaldehyde-Derived Dienamine as Dienophile in IEDDA Reaction

Contributor(s): Benjamin List, Saihu Liao
J.-L. Li, T.-R. Kang, S.-L. Zhou, R. Li, L. Wu, Y.-C. Chen*
Sichuan University, Chengdu, P. R. of China
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Publikationsdatum:
22. September 2010 (online)

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Significance

An organocatalytic asymmetric all-carbon-based inverse electron-demand Diels-­Alder reaction (IEDDA) of electron-deficient dienes 1 and crotonaldehyde 2 is reported. The dien­amine 5 generated in situ from crotonalydehyde and amine catalyst 3 acts as the dienophile and excellent β,γ-regioselectivities were observed. The corresponding cycloaddition products 4, highly functionalized cyclohexenes, are obtained in good yields with high diastereo- and enantioselectivity. Some further synthetic transformations of these cycloadducts were also explored.