Welcome to the new version of CaltechAUTHORS. Login is currently restricted to library staff. If you notice any issues, please email coda@library.caltech.edu
Published May 26, 2014 | Accepted Version + Supplemental Material
Journal Article Open

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.

Additional Information

© 2014 WILEY-VCH. Issue Online: 25 May 2014. Version of Record online: 08 April 2014. Manuscript revised: 17 February 2014. Manuscript received: 16 December 2013. We gratefully acknowledge NIHGMS (R01 GM104534) for financial support. H.M.N. would like to acknowledge the UNCF and Merck for generous funding. S.H.R. would like to acknowledge the Amgen Foundation for generous funding. We would like to thank Pascal Tripet for useful discussions.

Attached Files

Accepted Version - nihms602125.pdf

Supplemental Material - anie_201310905_sm_miscellaneous_information.pdf


Files (4.8 MB)
Name Size Download all
415.5 kB Preview Download
4.4 MB Preview Download

Additional details

August 22, 2023
October 23, 2023