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.
Department of Chemistry, University of California at Berkeley, Latimer Hall, Berkeley, CA (USA).
Hosea M
HM
Nelson
Solomon H
SH
Reisberg
Hunter P
HP
Shunatona
Jigar S
JS
Patel
F Dean
FD
Toste
D000838:Anions / Q000737:chemistry; D002384:Catalysis; D002412:Cations / Q000737:chemistry; D003500:Cyclization; D003979:Diazonium Compounds / Q000737:chemistry; D007211:Indoles / Q000138:chemical synthesis / Q000737:chemistry*; D011758:Pyrroles / Q000737:chemistry*; D013237:Stereoisomerism; D014363:Tryptamines / Q000737:chemistry
D000838:Anions; D002412:Cations; D003979:Diazonium Compounds; D007211:Indoles; D011758:Pyrroles; D014363:Tryptamines; C030820:tryptamine; C057812:indoline
amination; asymmetric catalysis; cyclization; phase-transfer catalysis; photolysis