Catalytic asymmetric synthesis of diarylacetates and 4,4-diarylbutanoates. A formal asymmetric synthesis of (+)-sertraline
Catalytic asymmetric synthesis of diarylacetates and 4,4-diarylbutanoates. A formal asymmetric synthesis of (+)-sertraline
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DOI：
10.1021/ol9905699
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发表时间：
1999-07-29
期刊：
影响因子：
5.2
通讯作者：
Hansen, T
中科院分区：
文献类型：
--
作者：
Davies, HML;Stafford, DG;Hansen, T
四元二钠催化苯基重氮乙酸酯(（S)-N（十二烷基苯磺酰）脯氨酸）(Rh-2（S- dosp)(4)）的分子间C-H插入化学反应可有效地在环己二烯上进行，导致二芳基乙酸酯的不对称合成。乙烯基重氮乙酸酯与环己二烯的反应产生了前所未有的类碳反应，这是一种碳氢插入/Cope重排的组合反应。这种新转化的合成效用通过其在形式不对称合成(+)-舍曲林中的应用得到了证明。
The intermolecular C-H insertion chemistry of phenyldiazoacetates catalyzed by dirhodium tetrakis((S)-N (dodecylbenzenesulfonyl)prolinate) (Rh-2(S-DOSP)(4)) can be effectively carried out on cyclohexadienes, leading to the asymmetric synthesis of diarylacetates. The reaction of vinyldiazoacetates with cyclohexadienes results in an unprecedented carbenoid reaction that is formally a combined C-H insertion/Cope rearrangement. The synthetic utility of this novel transformation was demonstrated by its utilization in a formal asymmetric synthesis of (+)-sertraline.