Sarpong, Richmond and Su, Julius T. and Stoltz, Brian M. (2003) The Development of a Facile Tandem Wolff/Cope Rearrangement for the Synthesis of Fused Carbocyclic Skeletons. Journal of the American Chemical Society, 125 (45). pp. 13624-13625. ISSN 0002-7863. doi:10.1021/ja037587c. https://resolver.caltech.edu/CaltechAUTHORS:20170215-143652773
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Abstract
A set of mild processes for the conversion of vinyl cyclopropyl diazo ketones to highly functionalized cycloheptadienones and vinyl cyclopentenones by use of a target-inspired tandem Wolff/Cope rearrangement sequence is described. A divergent reaction course of the vinyl cyclopropyl diazo ketone substrates under sono- or photochemical activation provides good to excellent yields (55−98%) of the product cycloheptadienones and vinyl cyclopentenones.
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| Additional Information: | © 2003 American Chemical Society. Received 29 July 2003. Published online 16 October 2003. Published in print 1 November 2003. We are grateful to Research Corporation, Pfizer·UNCF (postdoctoral fellowship to R.S.), and the NSF (predoctoral fellowship to J.T.S.) for generous financial support. We also thank Neil K. Garg for assisting with advanced NMR experiments. | |||||||||
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| Issue or Number: | 45 | |||||||||
| DOI: | 10.1021/ja037587c | |||||||||
| Record Number: | CaltechAUTHORS:20170215-143652773 | |||||||||
| Persistent URL: | https://resolver.caltech.edu/CaltechAUTHORS:20170215-143652773 | |||||||||
| Official Citation: | The Development of a Facile Tandem Wolff/Cope Rearrangement for the Synthesis of Fused Carbocyclic Skeletons Richmond Sarpong, Julius T. Su, and Brian M. Stoltz Journal of the American Chemical Society 2003 125 (45), 13624-13625 DOI: 10.1021/ja037587c | |||||||||
| Usage Policy: | No commercial reproduction, distribution, display or performance rights in this work are provided. | |||||||||
| ID Code: | 74335 | |||||||||
| Collection: | CaltechAUTHORS | |||||||||
| Deposited By: | Ruth Sustaita | |||||||||
| Deposited On: | 15 Feb 2017 22:53 | |||||||||
| Last Modified: | 11 Nov 2021 05:26 |
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