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.
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| 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. | ||||||||||||||
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| 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: | INVALID USER | ||||||||||||||
| Deposited On: | 02 Jul 2013 18:31 | ||||||||||||||
| Last Modified: | 09 Nov 2021 23:43 |
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