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3 article(s) from Crévisy, Christophe

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

Full text

Copper-catalyzed asymmetric conjugate addition of organometallic reagents to extended Michael acceptors

Thibault E. Schmid,
Sammy Drissi-Amraoui,
Christophe Crévisy,
Olivier Baslé and
Marc Mauduit

Beilstein J. Org. Chem. 2015, 11, 2418–2434, doi:10.3762/bjoc.11.263

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Graphical Abstract

Figure 1: Possible reaction pathways in conjugate additions of nucleophiles on extended Michael acceptors.

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Figure 2: Early reports of conjugate addition of copper-based reagents to extended Michael acceptors.

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Figure 3: First applications of copper catalyzed 1,6-ACA in total synthesis.

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Scheme 1: First example of enantioselective copper-catalyzed ACA on an extended Michael acceptor.

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Scheme 2: Meldrum’s acid derivatives as substrates in enantioselective ACA.

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Scheme 3: Reactivity of a cyclic dienone in Cu-catalyzed ACA of diethylzinc.

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Scheme 4: Efficiency of DiPPAM ligand in 1,6-ACA of dialkylzinc to cyclic dienones.

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Scheme 5: Sequential 1,6/1,4-ACA reactions involving linear aryldienones.

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Scheme 6: Unsymmetrical hydroxyalkyl NHC ligands in 1,6-ACA of cyclic dienones.

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Scheme 7: Performance of atropoisomeric diphosphines in 1,6-ACA of Et₂Zn on cyclic dienones.

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Scheme 8: Selective 1,6-ACA of Grignard reagents to acyclic dienoates, application in total synthesis.

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Scheme 9: Reactivity of polyenic linear thioesters towards sequential 1,6-ACA/reconjugation/1,4-ACA and produ...

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Scheme 10: 1,6-Conjugate addition of trialkylaluminium with regards to cyclic dienones.

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Scheme 11: Copper-catalyzed conjugate addition of trimethylaluminium onto nitro dienoates.

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Scheme 12: Copper-catalyzed selective 1,4-ACA in total synthesis of erogorgiaene.

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Scheme 13: 1,4-selective addition of diethylzinc onto a cyclic enynone catalyzed by a chiral NHC-based system.

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Scheme 14: Cu-NHC-catalyzed 1,6-ACA of dimethylzinc onto an α,β,γ,δ-unsaturated acyl-N-methylimidazole.

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Scheme 15: 1,4-Selectivity in conjugate addition on extended systems with the concomitant use of a chelating c...

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Scheme 16: Cu-NHC catalyzed 1,4-ACA as the key step in the total synthesis of ent-riccardiphenol B.

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Scheme 17: Cu-NHC-catalyzed 1,4-selective ACA reactions with enynones.

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Scheme 18: Linear dienones as substrates in 1,4-asymmetric conjugate addition reactions of Grignard reagents c...

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Scheme 19: 1,4-ACA of trimethylaluminium to a cyclic enynone catalyzed by a copper-NHC system.

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Scheme 20: Generation of a sterically encumbered chiral cyclohexanone from a polyunsaturated cyclic Michael ac...

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Scheme 21: Selective conversion of β,γ-unsaturated α-ketoesters in copper-catalyzed asymmetric conjugate addit...

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Scheme 22: Addition of trialkylaluminium compounds to nitroenynes catalyzed by L9/CuTC.

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Scheme 23: Addition of trialkylaluminium compounds to nitrodienes catalyzed by L9/CuTC.

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Scheme 24: Copper catalyzed 1,8- and 1,10-ACA reactions.

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Review

Published 03 Dec 2015

Full text

New library of aminosulfonyl-tagged Hoveyda–Grubbs type complexes: Synthesis, kinetic studies and activity in olefin metathesis transformations

Etienne Borré,
Frederic Caijo,
Christophe Crévisy and
Marc Mauduit

Beilstein J. Org. Chem. 2010, 6, 1159–1166, doi:10.3762/bjoc.6.132

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Graphical Abstract

Figure 1: Ruthenium precatalysts for olefin metathesis.

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Figure 2: Structure of precatalyst 3 and 4.

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Scheme 1: Synthesis of catalysts 4a–g.

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Figure 3: Kinetic studies of RCM of 8 (0.1 M) with precatalysts 4a–g (1 mol %) in CD₂Cl₂ at 30 °C.

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Full Research Paper

Published 06 Dec 2010

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