Direct Catalytic Asymmetric Vinylogous Conjugate Addition of Unsaturated Butyrolactones to α,β‐Unsaturated Thioamides |
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| Authors: | Dr. Liang Yin Dr. Hisashi Takada Shaoquan Lin Dr. Naoya Kumagai Prof. Dr. Masakatsu Shibasaki |
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| Affiliation: | 1. Institute of Microbial Chemistry (BIKAKEN), 3‐14‐23 Kamiosaki, Shinagawa‐ku, Tokyo 141‐0021 (Japan) http://www.bikaken.or.jp/research/group/shibasaki/shibasaki‐lab/index_e.html;2. JST, ACT‐C, 3‐14‐23 Kamiosaki, Shinagawa‐ku, Tokyo 141‐0021 (Japan) |
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| Abstract: | Soft Lewis acid/Brønsted base cooperative catalysts have enabled direct catalytic asymmetric vinylogous conjugate addition of α,β‐ and β,γ‐unsaturated butyrolactones to α,β‐unsaturated thioamides with perfect atom economy. When using α‐angelica lactone and its derivatives as pronucleophiles, as little as 0.5 mol % catalyst loading was sufficient to complete the reaction necessary to construct consecutive tri‐ and tetrasubstituted stereogenic centers in a highly diastereo‐ and enantioselective fashion. |
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| Keywords: | asymmetric catalysis copper heterocycles Michael addition synthetic methods |
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