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α-Diazo-β-ketonitriles: Uniquely Reactive Substrates for Arene and Alkene Cyclopropanation

Nani, Roger R. and Reisman, Sarah E. (2013) α-Diazo-β-ketonitriles: Uniquely Reactive Substrates for Arene and Alkene Cyclopropanation. Journal of the American Chemical Society, 135 (19). pp. 7304-7311. ISSN 0002-7863. doi:10.1021/ja401610p. https://resolver.caltech.edu/CaltechAUTHORS:20130701-134649902

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Abstract

An investigation of the intramolecular cyclopropanation reactions of α-diazo-β-ketonitriles is reported. These studies reveal that α-diazo-β-ketonitriles exhibit unique reactivity in their ability to undergo arene cyclopropanation reactions; other similar acceptor–acceptor-substituted diazo substrates instead produce mixtures of C–H insertion and dimerization products. α-Diazo-β-ketonitriles also undergo highly efficient intramolecular cyclopropanation of tri- and tetrasubstituted alkenes. In addition, the α-cyano-α-ketocyclopropane products are demonstrated to serve as substrates for S_(N)2, S_(N)2′, and aldehyde cycloaddition reactions.


Item Type:Article
Related URLs:
URLURL TypeDescription
http://dx.doi.org/10.1021/ja401610pDOIArticle
http://pubs.acs.org/doi/abs/10.1021/ja401610pPublisherArticle
ORCID:
AuthorORCID
Reisman, Sarah E.0000-0001-8244-9300
Additional Information:© 2013 American Chemical Society. Received: February 21, 2013; Published: May 3, 2013. We thank Prof. Brian Stoltz, Dr. Scott Virgil, and the Caltech Center for Catalysis and Chemical Synthesis for access to analytical equipment. We also thank Sigma-Aldrich for a kind donation of chemicals. S.E.R. is a fellow of the Alfred P. Sloan Foundation and a Camille Dreyfus Teacher-Scholar. Financial support from the National Science Foundation (CAREER-1057143), Boehringer-Ingleheim, Amgen, and the California Institute of Technology is gratefully acknowledged.
Funders:
Funding AgencyGrant Number
Alfred P. Sloan FoundationUNSPECIFIED
Camille and Henry Dreyfus FoundationUNSPECIFIED
NSFCHE-1057143
Boehringer-IngleheimUNSPECIFIED
AmgenUNSPECIFIED
CaltechUNSPECIFIED
Issue or Number:19
DOI:10.1021/ja401610p
Record Number:CaltechAUTHORS:20130701-134649902
Persistent URL:https://resolver.caltech.edu/CaltechAUTHORS:20130701-134649902
Official Citation:α-Diazo-β-ketonitriles: Uniquely Reactive Substrates for Arene and Alkene Cyclopropanation Roger R. Nani and Sarah E. Reisman Journal of the American Chemical Society 2013 135 (19), 7304-7311
Usage Policy:No commercial reproduction, distribution, display or performance rights in this work are provided.
ID Code:39168
Collection:CaltechAUTHORS
Deposited By: Jason Perez
Deposited On:02 Jul 2013 18:31
Last Modified:09 Nov 2021 23:43

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