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Mechanistic Insights into the Factors Determining Exo−EndoSelectivity in the Lewis Acid-Catalyzed Diels−Alder Reaction of 1,3-Dienes with 2-Cycloalkenones

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. 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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http://dx.doi.org/10.1021/ol0060026DOIArticle
ORCID:
AuthorORCID
Stoltz, Brian M.0000-0001-9837-1528
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
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:15 Jun 2020 20:22

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