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Chiral Anion Phase Transfer of Aryldiazonium Cations: An Enantioselective Synthesis of C3‐Diazenated Pyrroloindolines
Author(s) -
Nelson Hosea M.,
Reisberg Solomon H.,
Shunatona Hunter P.,
Patel Jigar S.,
Toste F. Dean
Publication year - 2014
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.201310905
Subject(s) - enantioselective synthesis , electrophile , chemistry , tryptamines , steric effects , yield (engineering) , tryptamine , phase (matter) , combinatorial chemistry , organic chemistry , catalysis , materials science , biochemistry , metallurgy
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.