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1 article(s) from Drissi-Amraoui, Sammy

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

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