Direct catalytic asymmetric aldol reaction of thioamides: a concise asymmetric synthesis of (R)-fluoxetine
Direct catalytic asymmetric aldol reaction of thioamides: a concise asymmetric synthesis of (R)-fluoxetine
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DOI：
10.1016/j.tetasy.2010.04.034
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发表时间：
2010-07-14
影响因子：
--
通讯作者：
Shibasaki, Masakatsu
中科院分区：
文献类型：
--
作者：
Iwata, Mitsutaka;Yazaki, Ryo;Shibasaki, Masakatsu
报道了芳香醛和硫代酰胺的直接催化不对称Aldol反应。(R，R)-Ph-BPE/[Cu(CH(3)CN)(4)]PF(6)/Li(OC(6)H(4)-p-OMe)组成的软Lewis酸/硬Bronsted碱协同催化剂有效地促进了标题反应，通过铜(I)与硫代酰胺的软软相互作用原位生成了活性硫代酰胺烯醇。羟醛产物转化为(R)-氟西汀，一种抗抑郁剂。(C)2010爱思唯尔有限公司。保留所有权利。
A direct catalytic asymmetric aldol reaction of aromatic aldehydes and thioamides is described. A soft Lewis acid/hard Bronsted base cooperative catalyst comprising (R,R)-Ph-BPE/[Cu(CH(3)CN)(4)]PF(6)/ Li(OC(6)H(4)-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. (C) 2010 Elsevier Ltd. All rights reserved.