Copper-Catalyzed Asymmetric Protoboration of β-Amidoacrylonitriles and β-Amidoacrylate Esters: An Efficient Approach to Functionalized Chiral α-Amino Boronate Esters
Copper-Catalyzed Asymmetric Protoboration of β-Amidoacrylonitriles and β-Amidoacrylate Esters: An Efficient Approach to Functionalized Chiral α-Amino Boronate Esters
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铜催化β-氨基丙烯腈和β-氨基丙烯酸酯的不对称原硼化反应：功能化手性α-氨基硼酸酯的有效方法
DOI：
10.1021/acs.orglett.7b01740
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发表时间：
2017-07-07
期刊：
影响因子：
5.2
通讯作者：
Xu, Senmiao
中科院分区：
文献类型：
--
作者：
Chen, Lili;Zou, Xiaoliang;Xu, Senmiao
首次报道了铜催化的双频哪醇二硼对Z-β-氨基丙烯腈和E-β-氨基丙烯酸乙酯的不对称硼氢化反应。该方法耐受大量的底物，在温和的反应条件下以良好的产率和对映选择性提供一系列稳定的官能化手性α-氨基硼酸酯。目前的方法也适用于克规模的合成没有侵蚀的对映选择性。本工作为手性α-氨基硼酸酯的合成提供了一种有吸引力的补充方法。
A copper-catalyzed asymmetric protoboration of both Z-beta-amidoacrylonitriles and ethyl E-beta-amidoacrylates using bis(pinacolato)diboron has been developed for the first time. The process tolerates a vast array of substrates, delivering a series of stable functionalized chiral alpha-amino boronate esters in good yields and enantioselectivities under mild reaction conditions. The current method is also applicable for gram-scale synthesis without erosion of enantioselectivity. This work provides an attractive and complementary approach to synthesizing enantioriched chiral alpha-amino boronate esters.