1,3-Rearrangement of ketene-N,O-acetals |
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| Authors: | Tatsuo SuzukiMasaharu Inui Seijiro HosokawaSusumu Kobayashi |
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| Institution: | a Faculty of Pharmaceutical Sciences, Tokyo University of Science, Ichigaya-Funagawara-machi, Shinjuku-ku, Tokyo 162-0826, Japan
b Frontier Research Center for Genomic Drug Discovery, Tokyo University of Science, Noda, Chiba 278-8510, Japan |
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| Abstract: | Ketene N,O-acetals were prepared stereoselectively and submitted to a Lewis acid-mediated 1,3-rearrangement to afford C-alkylated products. The reactions proceeded in a stereoselective manner to construct a chiral quaternary carbon in high selectivity. The stereochemistry of the quaternary center was found to be opposite to that obtained by an anionic direct dienolate alkylation. |
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