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Asymmetric Dearomatization via Cycloaddition Reaction

Reisman, Sarah E. and Kieffer, Madeleine E. and Wang, Haoxuan (2016) Asymmetric Dearomatization via Cycloaddition Reaction. In: Asymmetric Dearomatization Reactions. Wiley , pp. 153-174. ISBN 978-3-527-33851-1. https://resolver.caltech.edu/CaltechAUTHORS:20170713-103533853

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Abstract

This chapter covers recent advances in catalytic, asymmetric dearomatization reactions that proceed by cycloaddition. Despite its high stability, which renders it challenging to dearomatize via cycloaddition, Buchner and coworkers discovered the cyclopropanation of benzene in 1896. The unique chemistry of indoles, which possesses reactivity analogous to enamines but are hydrolytically stable, has resulted in their extensive use in the development of cycloaddition and formal cycloaddition reactions. Donor-acceptor cyclopropanes have also been explored as dipoles in asymmetric [3 + 2] cycloaddition reactions. Few examples of asymmetric dearomatization via [3 + 3] cycloaddition reactions have been reported in the literature. Metal-catalyzed carbenoid cyclopropanation has also been explored in heterocyclic arenes. Reiser and coworkers reported Cu/chiral bis(oxazoline)-catalyzed [2 + 1] enantioselective cycloadditions between acceptor-substituted carbenoids (diazoacetates 19 and 23) and furans 18 or W-Boc-pyrrole 22. Over the past three decades, significant progress has been made in the development of new, catalytic asymmetric cycloaddition reactions of arenes.


Item Type:Book Section
Related URLs:
URLURL TypeDescription
http://dx.doi.org/10.1002/9783527698479.ch7DOIArticle
http://onlinelibrary.wiley.com/doi/10.1002/9783527698479.ch7/summaryPublisherArticle
ORCID:
AuthorORCID
Reisman, Sarah E.0000-0001-8244-9300
Additional Information:© 2016 Wiley-VCH Verlag GmbH & Co. Published Online: 24 Jun 2016. Published Print: 6 Sep 2016.
Subject Keywords:asymmetric; catalysis; dearomatization; cycloaddition
Record Number:CaltechAUTHORS:20170713-103533853
Persistent URL:https://resolver.caltech.edu/CaltechAUTHORS:20170713-103533853
Official Citation:Reisman, S. E., Kieffer, M. E. and Wang, H. (2016) Asymmetric Dearomatization via Cycloaddition Reaction, in Asymmetric Dearomatization Reactions (ed S.-L. You), Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim, Germany. doi: 10.1002/9783527698479.ch7
Usage Policy:No commercial reproduction, distribution, display or performance rights in this work are provided.
ID Code:79078
Collection:CaltechAUTHORS
Deposited By: Ruth Sustaita
Deposited On:13 Jul 2017 20:00
Last Modified:03 Oct 2019 18:15

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