Enantioselective Epoxidation of 2,3-Disubstituted Naphthoquinones by a Side Chain Truncated Guanidine?Urea Bifunctional Organocatalyst
Enantioselective Epoxidation of 2,3-Disubstituted Naphthoquinones by a Side Chain Truncated Guanidine?Urea Bifunctional Organocatalyst
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侧链截短胍尿素双功能有机催化剂对2,3-二取代萘醌的对映选择性环氧化
DOI：
10.1021/acs.joc.0c02084
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发表时间：
2020
期刊：
影响因子：
--
通讯作者：
Nagasawa Kazuo
中科院分区：
文献类型：
--
作者：
Orihara Tatsuya;Kawaguchi Masaki;Hosoya Keisuke;Tsutsumi Ryosuke;Yamanaka Masahiro;Odagi Minami;Nagasawa Kazuo
基于DFT计算模型，设计了一种不含C2对称性的胍-脲双功能催化剂，用于叔丁基过氧化氢氧化2，3-二取代萘醌的不对称环氧化反应.本发明的有机催化反应提供了以高产率和高对映选择性（高达97：3 er）获得在C2和C3处带有芳基和甲基取代基的各种光学活性萘醌环氧化物的途径。
An organocatalytic enantioselective epoxidation of 2,3-disubstituted naphthoquinones withtert-butyl hydroperoxide as an oxidant was developed using a guanidine–urea bifunctional catalyst lackingC2symmetry, which was designed based upon the insights obtained from the DFT calculation model for our previousC2symmetric catalyst. The present organocatalytic reaction provides access to a variety of optically active naphthoquinone epoxides bearing aryl and methyl substituents at C2 and C3 in high yields with high enantioselectivities (up to 97:3 er).