Iridium-Catalyzed Diastereo- and Enantioselective [4+3] Cycloaddition of 4-Indolyl Allylic Alcohols with Azomethine Ylides
Iridium-Catalyzed Diastereo- and Enantioselective [4+3] Cycloaddition of 4-Indolyl Allylic Alcohols with Azomethine Ylides
复制标题
铱催化的非对映和对映选择性 [4 3] 4-吲哚基烯丙醇与甲亚碱叶立德的环加成反应
DOI：
10.1021/acs.orglett.0c04132
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发表时间：
2021-01-06
期刊：
影响因子：
5.2
通讯作者：
Deng, Wei-Ping
中科院分区：
文献类型：
--
作者：
Yang, Wu-Lin;Ni, Tao;Deng, Wei-Ping
报道了铱催化的4-吲哚烯丙醇与偶氮甲碱叶立德的不对称[4 + 3]环加成反应。酸促进剂三氟甲磺酸锌执行多种角色的能力是该策略成功的关键因素。该方法以良好的产率提供了可扩展的和有效的获得生物学上重要的氮杂卓并[3，4，5-cd]吲哚的途径，具有通常优异的非对映选择性和对映选择性（高达>20：1 dr和> 99%ee）。反应条件温和，底物和手性催化剂易得，底物范围广，突出了该方法的实用性。
An unprecedented iridium-catalyzed asymmetric [4 + 3] cycloaddition of racemic 4-indolyl allylic alcohols with azomethine ylides is reported. The ability of acid promoter zinc triflate to perform multiple roles is the key factor for the success of this strategy. This method provides scalable and efficient access to biologically important azepino[3,4,5-cd] indoles in good yields with generally excellent diastereo- and enantioselectivities (up to >20:1 dr and >99% ee). Mild reaction conditions, easily accessible substrates and chiral catalyst, and broad substrate scope highlight the practicality of this methodology.