Article ID | Journal | Published Year | Pages | File Type |
---|---|---|---|---|
5217773 | Tetrahedron | 2013 | 9 Pages |
Abstract
β-Enaminals were successfully synthesized in good to excellent yields by the reaction of C2-formylglycals with primary amines. Subsequent reaction with NaBH4 in HOAc led to unexpected reductive cleavage of allyl ether, i.e., the hydrodealkoxylation took place to produce the corresponding 3-deoxy-β-enaminals. In contrast, the reaction of β-enaminals with Zn/HOAc performed H4-elimination to afford a diene product. The result was attributed to the formation of a common eneiminium ion intermediate, and the different reduction reactivity.
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Related Topics
Physical Sciences and Engineering
Chemistry
Organic Chemistry
Authors
Zi-Ping Lin, Fung Fuh Wong, Yen-Bo Chen, Chun-Hung Lin, Min-Tsang Hsieh, Jin-Cherng Lien, Yin-Hsuan Chou, Hui-Chang Lin,