Chiral Anion Phase Transfer of Aryldiazonium Cations: An Enantioselective Synthesis of C3‐Diazenated Pyrroloindolines1. Issue 22 (8th April 2014)

• Record Type: Journal Article
• Authors: Nelson, Hosea M.; Reisberg, Solomon H.; Shunatona, Hunter P.; Patel, Jigar S.; Toste, F. Dean
• Is Part Of: Angewandte Chemie international edition. Volume 53:Issue 22(2014)
• Page Start: 5600
• Page End: 5603
• Publication Date: 2014-04-08
• Subjects: Chemistry -- Periodicals; 540
• DOI: 10.1002/anie.201310905
• Languages: English
• ISSNs: 1433-7851

Abstract

<abstract abstract-type="main" xml:lang="en"> <title>Abstract</title> <p>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 % <italic>ee</italic>. The air‐ and water‐tolerant reaction allows electronic and steric diversity of the aryldiazonium electrophile and the tryptamine core.</p> </abstract>