Organic Letters
Organic Letters
5 years ago

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
Sk Mohammad Aziz, Saumen Hajra, Somnath Singha Roy, Dhiraj Das
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).

Publisher URL: http://dx.doi.org/10.1021/acs.orglett.7b01833

DOI: 10.1021/acs.orglett.7b01833

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