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1 article(s) from Morvan, Jennifer

Copper-catalyzed enantioselective conjugate addition of organometallic reagents to challenging Michael acceptors

Delphine Pichon,
Jennifer Morvan,
Christophe Crévisy and
Marc Mauduit

Beilstein J. Org. Chem. 2020, 16, 212–232, doi:10.3762/bjoc.16.24

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Graphical Abstract

Scheme 1: Competitive side reactions in the Cu ECA of organometallic reagents to α,β-unsaturated aldehydes.

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Scheme 2: Cu-catalyzed ECA of α,β-unsaturated aldehydes with phosphoramidite- (a) and phosphine-based ligands...

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Scheme 3: One-pot Cu-catalyzed ECA/organocatalyzed α-substitution of enals.

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Scheme 4: Combination of copper and amino catalysis for enantioselective β-functionalizations of enals.

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Scheme 5: Optimized conditions for the Cu ECAs of R₂Zn, RMgBr, and AlMe₃ with α,β-unsaturated aldehydes.

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Scheme 6: CuECA of Grignard reagents to α,β-unsaturated thioesters and their application in the asymmetric to...

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Scheme 7: Improved Cu ECA of Grignard reagents to α,β-unsaturated thioesters, and their application in the as...

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Scheme 8: Catalytic enantioselective synthesis of vicinal dialkyl arrays via Cu ECA of Grignard reagents to γ...

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Scheme 9: 1,6-Cu ECA of MeMgBr to α,β,γ,δ-bisunsaturated thioesters: an iterative approach to deoxypropionate...

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Scheme 10: Tandem Cu ECA/intramolecular enolate trapping involving 4-chloro-α,β-unsaturated thioester 22.

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Scheme 11: Cu ECA of Grignard reagents to 3-boronyl α,β-unsaturated thioesters.

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Scheme 12: Cu ECA of alkylzirconium reagents to α,β-unsaturated thioesters.

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Scheme 13: Conversion of acylimidazoles into aldehydes, ketones, acids, esters, amides, and amines.

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Scheme 14: Cu ECA of dimethyl malonate to α,β-unsaturated acylimidazole 31 with triazacyclophane-based ligand ...

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Scheme 15: Cu/L13-catalyzed ECA of alkylboranes to α,β-unsaturated acylimidazoles.

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Scheme 16: Cu/hydroxyalkyl-NHC-catalyzed ECA of dimethylzinc to α,β-unsaturated acylimidazoles.

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Scheme 17: Stereocontrolled synthesis of 3,5,7-all-syn and anti,anti-stereotriads via iterative Cu ECAs.

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Scheme 18: Stereocontrolled synthesis of anti,syn- and anti,anti-3,5,7-(Me,OR,Me) units via iterative Cu ECA/B...

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Scheme 19: Cu-catalyzed ECA of dialkylzinc reagents to α,β-unsaturated N-acyloxazolidinones.

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Scheme 20: Cu/phosphoramidite L16-catalyzed ECA of dialkylzincs to α,β-unsaturated N-acyl-2-pyrrolidinones.

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Scheme 21: Cu/(R,S)-Josiphos (L9)-catalyzed ECA of Grignard reagents to α,β-unsaturated amides.

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Scheme 22: Cu/Josiphos (L9)-catalyzed ECA of Grignard reagents to polyunsaturated amides.

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Scheme 23: Cu-catalyzed ECA of trimethylaluminium to N-acylpyrrole derivatives.

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Review

Published 17 Feb 2020

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