NDLI: Mechanistic Investigations into the Enantioselective Conia-Ene Reaction Catalyzed by Cinchona-Derived Amino Urea Pre-Catalysts and $Cu^{I}$

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Mechanistic Investigations into the Enantioselective Conia-Ene Reaction Catalyzed by Cinchona-Derived Amino Urea Pre-Catalysts and $Cu^{I}$

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Mechanistic Investigations into the Enantioselective Conia-Ene Reaction Catalyzed by Cinchona-Derived Amino Urea Pre-Catalysts and $Cu^{I}$

Content Provider	World Health Organization (WHO)-Global Index Medicus
Author	Ferrali, Alessandro Ortín, Irene Yang, Ting Paton, Robert S. Dixon, Darren J. Fuentes De Arriba, Ángel L. Sladojevich, Filippo
Description	Author Affiliation: Sladojevich F ( Chemistry Research Laboratory, Department of Chemistry, University of Oxford, Mansfield Road, Oxford, OX1 3TA (U.K.).)
Abstract	The enantioselective Conia-ene cyclization of alkyne-tethered β-ketoesters is efficiently catalyzed by the combination of cinchona-derived amino-urea pre-catalysts and copper(I) salts. The reaction scope is broad and a series of substrates can be efficiently cyclized with high yields and enantioselectivities. Herein, we present a detailed mechanistic study based on experimental considerations and quantum mechanical calculations. Several variables, such as the nature of the organic pre-catalyst and the metal-ion source, have been thoroughly investigated. Kinetic studies, as well as kinetic isotope effects and deuterium labeling experiments have been used to gain further insights into the mechanism and prove the cooperative nature of the catalytic system. Our studies suggest that the rate-limiting step for the reaction involves the β-ketoester deprotonation and that the active species responsible for the enantiodeterming step is monomeric in amino-urea pre-catalyst. Computational studies provide a quantitative understanding of the observed stereoinduction and identify hydrogen bonding from the urea group as a crucial factor in determining the observed enantioselectivity.
ISSN	09476539
e-ISSN	15213765
Journal	Chemistry - A European Journal
Issue Number	42
Volume Number	19
Language	English
Publisher	Wiley-VCH;ChemPubSoc Europe
Publisher Date	2013-10-11
Publisher Place	Germany
Access Restriction	Open
Subject Keyword	Cinchona Alkaloids Chemistry Cinchona Copper Urea Catalysis Cyclization Molecular Structure Quantum Theory Stereoisomerism Research Support, Non-U.S. Gov't
Content Type	Text
Resource Type	Article
Subject	Organic Chemistry Catalysis

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