Efficient synthesis of trifluoromethyl and related trisubstituted alkene dipeptide isosteres by palladium-catalyzed carbonylation of amino acid derived allylic carbonates
Efficient synthesis of trifluoromethyl and related trisubstituted alkene dipeptide isosteres by palladium-catalyzed carbonylation of amino acid derived allylic carbonates
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DOI：
10.1021/jo702318d
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发表时间：
2008-05-16
影响因子：
3.6
通讯作者：
Fujii, Nobutaka
中科院分区：
文献类型：
--
作者：
Inokuchi, Eriko;Narumi, Tetsuo;Fujii, Nobutaka
报道了一种立体选择性合成（Z）-三氟甲基烯二肽电子等排体（CF（3）-ADI）的新方法。以易得的N-BOC-L-苯丙氨酸为原料，在钯催化下，烯丙基碳酸酯发生羰基化反应，得到Phe-Gly型CF（3）-ADI，N-Boc衍生物的反应产率高，但立体选择性较低（E：Z = 62：38-43：57），而NN-diBoc衍生物的反应只得到所需的（Z）-异构体，产率为61%。我们还提出了一个高立体选择性的合成Phe-Gly型三取代烯烃二肽电子等排体的钯催化羰基化。
A novel stereoselective synthetic approach to (Z)-trifluoromethylalkene dipeptide isosteres (CF(3)-ADIs) is described. Starting from readily available N-BOC-L-phenylalanine, Phe-Gly type CF(3)-ADIs were obtained through palladium-catalyzed carbonylation of allylic carbonates under CO. While the reaction of N-Boc derivatives proceeds in excellent yields but lower stereoselectivity (E:Z = 62:38-43:57), the reaction of the NN-diBoc derivative exclusively affords the desired (Z)-isomer in 61% yield. We also present a highly stereoselective synthesis of several Phe-Gly type trisubstituted alkene dipeptide isosteres by palladium-catalyzed carbonylation.