Construction of Quaternary Stereogenic Carbon Centers through Copper-Catalyzed Enantioselective Allylic Alkylation of Azoles

Construction of Quaternary Stereogenic Carbon Centers through Copper-Catalyzed Enantioselective Allylic Alkylation of Azoles
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DOI:
10.1002/anie.201600619
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发表时间:
2016-04-04
影响因子:
16.6
通讯作者:
Sawamura, Masaya
Sawamura, Masaya
中科院分区:
化学1区
文献类型:
--
作者:
Ohmiya, Hirohisa;Zhang, Heng;Sawamura, Masaya

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利用一种新的带有萘酚羟基的手性N-杂环卡宾配体,实现了铜催化的唑类化合物与,-二取代伯烯丙基磷酸酯的不对称烯丙基烷基化反应。该反应具有优异的分支区域选择性和高的对映选择性,从而在杂芳环的位置处形成受控的全碳季立体中心。
Copper-catalyzed enantioselective allylic alkylation of azoles with ,-disubstituted primary allylic phosphates was achieved using a new chiral N-heterocyclic carbene ligand bearing a naphtholic hydroxy group. This reaction occurred with excellent branch regioselectivity and high enantioselectivity, thus forming a controlled all-carbon quaternary stereogenic center at the position to the heteroaromatic ring.