Synthesis of Chiral α,β-Unsaturated γ‑Amino Esters via Pd-Catalyzed Asymmetric Allylic Amination
Synthesis of Chiral α,β-Unsaturated γ‑Amino Esters via Pd-Catalyzed Asymmetric Allylic Amination
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Pd催化不对称烯丙基胺化合成手性α,β-不饱和γ-氨基酯
DOI：
10.1021/acs.orglett.7b01904
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发表时间：
2017
期刊：
影响因子：
5.2
通讯作者：
Chao Xia Jiefeng Shen Delong Liu Wanbin Zhang
中科院分区：
文献类型：
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作者：
Chao Xia Jiefeng Shen Delong Liu Wanbin Zhang
本文报道了钯催化的4-取代2-乙酰氧基丁-3-烯酸酯与胺的不对称烯丙基胺化反应，用于手性α，β-不饱和γ-氨基酯的区域专一性合成。手性胺化产物的收率可达98%，ee值可达99%，并可方便地转化为手性γ-氨基酸/醇衍生物和手性γ-内酰胺类化合物，进而可用于多种手性药物和候选药物的合成。手性γ-氨基酯的优先生成可能归因于烯丙基底物右侧的大体积取代基。本工作为手性α，β-不饱和γ-氨基酯及其衍生物的合成提供了一种有效的方法。
A Pd-catalyzed asymmetric allylic amination of 4-substituted 2-acetoxybut-3-enoates with amines has been developed for the regiospecific synthesis of chiral α,β-unsaturated γ-amino esters. The desired chiral aminated products can be obtained in up to 98% yield, and 99% ee and can be conveniently transformed to chiral γ-amino acid/alcohol derivatives and chiral γ-lactams, which can then be subjected to the synthesis of several types of chiral drugs and drug candidates. The preferential formation of chiral γ-amino esters may be attributed to the bulky substituents on the right side of the allyl substrates. This work provides an efficient strategy for the synthesis of chiral α,β-unsaturated γ-amino esters and their derivatives.