Ontology highlight
ABSTRACT:
SUBMITTER: Nelson HM
PROVIDER: S-EPMC4109272 | biostudies-literature | 2014 May
REPOSITORIES: biostudies-literature
Nelson Hosea M HM Reisberg Solomon H SH Shunatona Hunter P HP Patel Jigar S JS Toste F Dean FD
Angewandte Chemie (International ed. in English) 20140408 22
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 c ...[more]