Published May 15, 2013
| Version Supplemental Material
Journal Article
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α-Diazo-β-ketonitriles: Uniquely Reactive Substrates for Arene and Alkene Cyclopropanation
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.
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.Attached Files
Supplemental Material - ja401610p_si_001.pdf
Supplemental Material - ja401610p_si_002.pdf
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ja401610p_si_001.pdf
Additional details
Identifiers
- Eprint ID
- 39168
- DOI
- 10.1021/ja401610p
- Resolver ID
- CaltechAUTHORS:20130701-134649902
Funding
- Alfred P. Sloan Foundation
- Camille and Henry Dreyfus Foundation
- NSF
- CHE-1057143
- Boehringer-Ingleheim
- Amgen
- Caltech
Dates
- Created
-
2013-07-02Created from EPrint's datestamp field
- Updated
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2021-11-09Created from EPrint's last_modified field