Chiral anion phase transfer of aryldiazonium cations: an enantioselective synthesis of C3-diazenated pyrroloindolines.
Herein is reported the first asymmetric utilization of aryldiazonium cations as a source of electrophilic nitrogen. This is achieved through a chiral anion phase-transfer pyrroloindolinization reaction that forms C3-diazenated pyrroloindolines from simple tryptamines and aryldiazonium tetrafluoroborates. The title compounds are obtained in up to 99% yield and 96% ee. The air- and water-tolerant reaction allows electronic and steric diversity of the aryldiazonium electrophile and the tryptamine core.
['Nelson|Hosea M|HM|', 'Reisberg|Solomon H|SH|', 'Shunatona|Hunter P|HP|', 'Patel|Jigar S|JS|', 'Toste|F Dean|FD|']
D000838:Anions D002384:Catalysis D002412:Cations D003500:Cyclization D003979:Diazonium Compounds D007211:Indoles D011758:Pyrroles D013237:Stereoisomerism D014363:Tryptamines
amination asymmetric catalysis cyclization phase-transfer catalysis photolysis