Catalyst-Free "On-Water" Regio-and Stereospecific Ring-Opening of Spiroaziridine Oxindole: Enantiopure Synthesis of Unsymmetrical 3,3'-Bisindoles

Catalyst-Free "On-Water" Regio-and Stereospecific Ring-Opening of Spiroaziridine Oxindole: Enantiopure Synthesis of Unsymmetrical 3,3'-Bisindoles
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DOI:
10.1021/acs.orglett.7b01833
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发表时间:
2017-08-04
期刊:
影响因子:
5.2
通讯作者:
Das, Dhiraj
Das, Dhiraj
中科院分区:
化学1区
文献类型:
--
作者:
Hajra, Saumen;Roy, Somnath Singha;Das, Dhiraj

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在无催化剂条件下,水介导的非外消旋螺氮丙啶、羟吲哚和吲哚的区域和立体特异性开环反应保持了构型。该方法提供了直接获得对映体纯的3,3 '-混合双吲哚的方法,具有优异的产率和对映体选择性(高达98%ee)。
A catalyst-free water-mediated regio- and stereospecific ring-opening reaction of nonracemic spiroaziridine oxindoles and indoles has been developed with retention of configuration. This method provides direct access to enantiopure 3,3'-mixed bisindoles with excellent yield and enantioselectivity (up to 98% ee).