Asymmetric Sequential Cu-Catalyzed 1,6/1,4-Conjugate Additions of Hard Nucleophiles to Cyclic Dienones: Determination of Absolute Configurations and Origins of Enantioselectivity.
Identifieur interne : 000B46 ( PubMed/Corpus ); précédent : 000B45; suivant : 000B47Asymmetric Sequential Cu-Catalyzed 1,6/1,4-Conjugate Additions of Hard Nucleophiles to Cyclic Dienones: Determination of Absolute Configurations and Origins of Enantioselectivity.
Auteurs : Charlie Blons ; Marie S T. Morin ; Thibault E. Schmid ; Thomas Vives ; Sophie Colombel-Rouen ; Olivier Baslé ; Thibault Reynaldo ; Cody L. Covington ; Stéphanie Halbert ; Sean N. Cuskelly ; Paul V. Bernhardt ; Craig M. Williams ; Jeanne Crassous ; Prasad L. Polavarapu ; Christophe Crévisy ; Hélène Gérard ; Marc MauduitSource :
- Chemistry (Weinheim an der Bergstrasse, Germany) [ 1521-3765 ] ; 2017.
Abstract
The first stereocontrolled Cu-catalyzed sequential 1,6/1,4-asymmetric conjugate addition (ACA) of C-metalated hard nucleophiles to cyclic dienones is reported. The use of DiPPAM (diphenylphosphinoazomethinylate) followed by a phosphoramidite as the stereoinducing ligands facilitated both high ee values for the 1,6-ACA and high de values for the 1,4-ACA reaction components, which thus gave enantioenriched 1,3-dialkylated moieties. The absolute configurations were determined by using vibrational circular dichroism (VCD) and optical rotatory dispersion (ORD) spectroscopy, in combination with DFT calculations and X-ray analysis. Interestingly, DFT calculations for the mechanism of enantioselective 1,6-addition by using an unprecedented Cu-Zn bimetallic catalytic system confirmed this attribution. Lastly, exploring intramolecular cyclization avenues for enantioenriched 1,3-dialkylated products provided access to the challenging drimane skeleton.
DOI: 10.1002/chem.201606034
PubMed: 28370488
Links to Exploration step
pubmed:28370488Le document en format XML
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<sourceDesc><biblStruct><analytic><title xml:lang="en">Asymmetric Sequential Cu-Catalyzed 1,6/1,4-Conjugate Additions of Hard Nucleophiles to Cyclic Dienones: Determination of Absolute Configurations and Origins of Enantioselectivity.</title>
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<author><name sortKey="Halbert, Stephanie" sort="Halbert, Stephanie" uniqKey="Halbert S" first="Stéphanie" last="Halbert">Stéphanie Halbert</name>
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<author><name sortKey="Polavarapu, Prasad L" sort="Polavarapu, Prasad L" uniqKey="Polavarapu P" first="Prasad L" last="Polavarapu">Prasad L. Polavarapu</name>
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<front><div type="abstract" xml:lang="en">The first stereocontrolled Cu-catalyzed sequential 1,6/1,4-asymmetric conjugate addition (ACA) of C-metalated hard nucleophiles to cyclic dienones is reported. The use of DiPPAM (diphenylphosphinoazomethinylate) followed by a phosphoramidite as the stereoinducing ligands facilitated both high ee values for the 1,6-ACA and high de values for the 1,4-ACA reaction components, which thus gave enantioenriched 1,3-dialkylated moieties. The absolute configurations were determined by using vibrational circular dichroism (VCD) and optical rotatory dispersion (ORD) spectroscopy, in combination with DFT calculations and X-ray analysis. Interestingly, DFT calculations for the mechanism of enantioselective 1,6-addition by using an unprecedented Cu-Zn bimetallic catalytic system confirmed this attribution. Lastly, exploring intramolecular cyclization avenues for enantioenriched 1,3-dialkylated products provided access to the challenging drimane skeleton.</div>
</front>
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<Abstract><AbstractText>The first stereocontrolled Cu-catalyzed sequential 1,6/1,4-asymmetric conjugate addition (ACA) of C-metalated hard nucleophiles to cyclic dienones is reported. The use of DiPPAM (diphenylphosphinoazomethinylate) followed by a phosphoramidite as the stereoinducing ligands facilitated both high ee values for the 1,6-ACA and high de values for the 1,4-ACA reaction components, which thus gave enantioenriched 1,3-dialkylated moieties. The absolute configurations were determined by using vibrational circular dichroism (VCD) and optical rotatory dispersion (ORD) spectroscopy, in combination with DFT calculations and X-ray analysis. Interestingly, DFT calculations for the mechanism of enantioselective 1,6-addition by using an unprecedented Cu-Zn bimetallic catalytic system confirmed this attribution. Lastly, exploring intramolecular cyclization avenues for enantioenriched 1,3-dialkylated products provided access to the challenging drimane skeleton.</AbstractText>
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