Ge, Min and Stoltz, Brian M. and Corey, E. J. (2000) Mechanistic Insights into the Factors Determining Exo−EndoSelectivity in the Lewis Acid-Catalyzed Diels−Alder Reaction of 1,3-Dienes with 2-Cycloalkenones. Organic Letters, 2 (13). pp. 1927-1929. ISSN 1523-7060. doi:10.1021/ol0060026. https://resolver.caltech.edu/CaltechAUTHORS:20170222-101505337
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Abstract
We adduce evidence that the asynchronous, Lewis acid-catalyzed Diels−Alder reaction of 2-cycloalkenones with nonsimple α,β-enones can proceed via transition states in which the 1,3-diene subunit is skewed, i.e., nonplanar, with profound effects on the ratio of exo and endo addition products.
| Item Type: | Article | ||||||
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| Additional Information: | © 2000 American Chemical Society. Received 1 May 2000. Published online 27 May 2000. Published in print 1 June 2000. This research was assisted financially by a grant from the National Institutes of Health. | ||||||
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| Issue or Number: | 13 | ||||||
| DOI: | 10.1021/ol0060026 | ||||||
| Record Number: | CaltechAUTHORS:20170222-101505337 | ||||||
| Persistent URL: | https://resolver.caltech.edu/CaltechAUTHORS:20170222-101505337 | ||||||
| Official Citation: | Mechanistic Insights into the Factors Determining Exo−Endo Selectivity in the Lewis Acid-Catalyzed Diels−Alder Reaction of 1,3-Dienes with 2-Cycloalkenones Min Ge, Brian M. Stoltz, and E. J. Corey Organic Letters 2000 2 (13), 1927-1929 DOI: 10.1021/ol0060026 | ||||||
| Usage Policy: | No commercial reproduction, distribution, display or performance rights in this work are provided. | ||||||
| ID Code: | 74464 | ||||||
| Collection: | CaltechAUTHORS | ||||||
| Deposited By: | Ruth Sustaita | ||||||
| Deposited On: | 22 Feb 2017 23:04 | ||||||
| Last Modified: | 11 Nov 2021 05:27 |
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