Chiral Anion Phase Transfer of Aryldiazonium Cations: An Enantioselective Synthesis of C3??Diazenated Pyrroloindolines

…, SH Reisberg, HP Shunatona, JS Patel…

Index: Nelson, Hosea M.; Reisberg, Solomon H.; Shunatona, Hunter P.; Patel, Jigar S.; Toste, F. Dean Angewandte Chemie - International Edition, 2014 , vol. 53, # 22 p. 5600 - 5603 Angew. Chem., 2014 , vol. 126, # 22 p. 5706 - 5709,4

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Citation Number: 28

Abstract

Abstract 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 ...