Direct catalytic asymmetric aldol reaction of thioamides: a concise asymmetric synthesis of (R)-fluoxetine |
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Authors: | Mitsutaka Iwata Ryo Yazaki Naoya Kumagai Masakatsu Shibasaki |
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Institution: | 1. Microbial Chemistry Research Foundation, Microbial Chemistry Research Center, 3-14-23 Kamioosaki, Shinagawa-ku, Tokyo 141-0021, Japan;2. Graduate School of Pharmaceutical Sciences, The University of Tokyo, 7-3-1 Hongo, Bunkyo-ku, Tokyo 113-0033, Japan |
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Abstract: | A direct catalytic asymmetric aldol reaction of aromatic aldehydes and thioamides is described. A soft Lewis acid/hard Brønsted base cooperative catalyst comprising (R,R)-Ph-BPE/Cu(CH3CN)4]PF6/Li(OC6H4-p-OMe) promoted the title reaction efficiently, triggered by in situ generation of the active thioamide enolate through a soft–soft interaction of Cu(I) and the thioamide. The aldol product was transformed into (R)-fluoxetine, an antidepressant agent. |
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