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Catalytic Enantioselective Decarboxylative Protonation

Mohr, Justin T. and Nishimata, Toyoki and Behenna, Douglas C. and Stoltz, Brian M. (2006) Catalytic Enantioselective Decarboxylative Protonation. Journal of the American Chemical Society, 128 (35). pp. 11348-11349. ISSN 0002-7863. https://resolver.caltech.edu/CaltechAUTHORS:20170222-073849342

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Abstract

We report a highly enantioselective, general catalytic system for the facile synthesis of tertiary stereocenters by protonation adjacent to cyclic ketones. The method relies on catalytic decarboxylative protonation of readily accessible racemic quaternary β-ketoesters. A range of substituted cycloalkanone compounds can be accessed through this process with high levels of enantioselectivity.


Item Type:Article
Related URLs:
URLURL TypeDescription
http://dx.doi.org/10.1021/ja063335aDOIArticle
http://pubs.acs.org/doi/suppl/10.1021/ja063335aRelated ItemSupporting Information
ORCID:
AuthorORCID
Mohr, Justin T.0000-0002-7005-3322
Stoltz, Brian M.0000-0001-9837-1528
Additional Information:© 2006 American Chemical Society. Received 17 May 2006. Published online 15 August 2006. Published in print 1 September 2006. The authors thank Eli Lilly (predoctoral fellowship to J.T.M.), Sankyo Co., Ltd. (financial support of T.N.), The Fannie and John Hertz Foundation (predoctoral fellowship to D.C.B.), Merck, Amgen, Johnson & Johnson, Bristol-Myers Squibb, and the Dreyfus Foundation for generous funding.
Funders:
Funding AgencyGrant Number
Sankyo Co., Ltd.UNSPECIFIED
Fannie and John Hertz FoundationUNSPECIFIED
MerckUNSPECIFIED
AmgenUNSPECIFIED
Johnson and JohnsonUNSPECIFIED
Bristol-Myers SquibbUNSPECIFIED
Camille and Henry Dreyfus FoundationUNSPECIFIED
Issue or Number:35
Record Number:CaltechAUTHORS:20170222-073849342
Persistent URL:https://resolver.caltech.edu/CaltechAUTHORS:20170222-073849342
Official Citation:Catalytic Enantioselective Decarboxylative Protonation Justin T. Mohr, Toyoki Nishimata, Douglas C. Behenna, and Brian M. Stoltz Journal of the American Chemical Society 2006 128 (35), 11348-11349 DOI: 10.1021/ja063335a
Usage Policy:No commercial reproduction, distribution, display or performance rights in this work are provided.
ID Code:74447
Collection:CaltechAUTHORS
Deposited By: Ruth Sustaita
Deposited On:22 Feb 2017 19:50
Last Modified:15 Jun 2020 20:06

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