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

Nelson, Hosea M. and Reisberg, Solomon H. and Shunatona, Hunter P. and Patel, Jigar S. and Toste, F. Dean (2014) Chiral Anion Phase Transfer of Aryldiazonium Cations: An Enantioselective Synthesis of C3-Diazenated Pyrroloindolines. Angewandte Chemie International Edition, 53 (22). pp. 5600-5603. ISSN 1433-7851. PMCID PMC4109272. doi:10.1002/anie.201310905. https://resolver.caltech.edu/CaltechAUTHORS:20210811-225352282

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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 diversity of the aryldiazonium electrophile and the tryptamine core.


Item Type:Article
Related URLs:
URLURL TypeDescription
https://doi.org/10.1002/anie.201310905DOIArticle
http://www.ncbi.nlm.nih.gov/pmc/articles/pmc4109272/PubMed CentralArticle
ORCID:
AuthorORCID
Nelson, Hosea M.0000-0002-4666-2793
Reisberg, Solomon H.0000-0003-0017-3414
Toste, F. Dean0000-0001-8018-2198
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.
Funders:
Funding AgencyGrant Number
NIHR01 GM104534
United Negro College FundUNSPECIFIED
MerckUNSPECIFIED
AmgenUNSPECIFIED
Subject Keywords:amination; asymmetric catalysis; cyclization; phase-transfer catalysis; photolysis
Issue or Number:22
PubMed Central ID:PMC4109272
DOI:10.1002/anie.201310905
Record Number:CaltechAUTHORS:20210811-225352282
Persistent URL:https://resolver.caltech.edu/CaltechAUTHORS:20210811-225352282
Official Citation:Nelson, H.M., Reisberg, S.H., Shunatona, H.P., Patel, J.S. and Toste, F.D. (2014), Chiral Anion Phase Transfer of Aryldiazonium Cations: An Enantioselective Synthesis of C3-Diazenated Pyrroloindolines. Angew. Chem. Int. Ed., 53: 5600-5603. https://doi.org/10.1002/anie.201310905
Usage Policy:No commercial reproduction, distribution, display or performance rights in this work are provided.
ID Code:110222
Collection:CaltechAUTHORS
Deposited By: George Porter
Deposited On:12 Aug 2021 16:30
Last Modified:12 Aug 2021 16:30

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