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Asymmetric Synthesis of Quaternary Stereocenters via Metal Enolates

Korch, Katerina M. and Loskot, Steven A. and Stoltz, Brian M. (2016) Asymmetric Synthesis of Quaternary Stereocenters via Metal Enolates. In: PATAI'S Chemistry of Functional Groups. Wiley , Chichester, pp. 1-85. ISBN 9780470682531. https://resolver.caltech.edu/CaltechAUTHORS:20170919-091408635

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Abstract

The strategy of using chiral metal enolate intermediates in a diverse variety of asymmetric transformations has allowed the generation of quaternary stereocenter-bearing products that are otherwise difficult to access. Many classic transformations including aldol, Mannich, conjugate addition, alkylation, and pericyclic-type reactions, as well as allylic alkylation and α-arylation/alkenylation, have been adapted to proceed through chiral metal enolate intermediates, allowing the asymmetric synthesis of many complex products in both an intermolecular and intramolecular manner. These transformations have proven useful in the synthesis of natural products and may also be applied to the synthesis of novel pharmaceuticals and other compounds of interest in the future. This review includes work done up to and including the year 2014.


Item Type:Book Section
Related URLs:
URLURL TypeDescription
https://doi.org/10.1002/9780470682531.pat0858DOIArticle
http://onlinelibrary.wiley.com/doi/10.1002/9780470682531.pat0858/abstractPublisherArticle
ORCID:
AuthorORCID
Stoltz, Brian M.0000-0001-9837-1528
Additional Information:© 2016 John Wiley & Sons, Ltd. Published Online: 15 SEP 2017.
Subject Keywords:asymmetric synthesis; enantioselective synthesis; quaternary stereocenter; aldol reaction; Mannich reaction; conjugate addition; allylic alkylation; alkylation;α-arylation; α-alkenylation; pericyclic reactions; Claisen reactions; Conia-ene reaction
Record Number:CaltechAUTHORS:20170919-091408635
Persistent URL:https://resolver.caltech.edu/CaltechAUTHORS:20170919-091408635
Usage Policy:No commercial reproduction, distribution, display or performance rights in this work are provided.
ID Code:81560
Collection:CaltechAUTHORS
Deposited By: Tony Diaz
Deposited On:19 Sep 2017 16:23
Last Modified:03 Oct 2019 18:44

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