Organocatalytic γ-oxidation of α,β-unsaturated aldehydes

Chromiński, Mikołaj; Giedyk, Maciej; Gryko, Dorota

doi:10.3998/ark.5550190.p008.394

Cited by 3 publications

(1 citation statement)

References 22 publications

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“…We first started our investigations into the feasibility of a selective dienamine-catalyzed process for the γ-oxygenation of enals. Unfortunately, as in previous works, 7 all our efforts were unsuccessful to afford the desired γ-functionalized product, even in the case of α-hindered enals. These results showed that dienamine catalysis cannot be the solution to all the problems faced in the field of γ-functionalization of enals.…”

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confidence: 77%

Highly selective γ-alkoxylation, γ-amination and γ-alkylation of unbiased enals by means of photoredox catalysis

2023

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mentioning

confidence: 77%

Highly selective γ-alkoxylation, γ-amination and γ-alkylation of unbiased enals by means of photoredox catalysis

2023

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Asymmetric α-Selective and Remote γ-Selective Functionalization of Enals and Enones Through Serebryakov–Jørgensen Dienamines (1-Aminobuta-1,3-Dienes)

Anebouselvy

Ramachary

2018

Dienamine Catalysis for Organic Synthesis

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Serebryakov–Jørgensen dienamine intermediates derived from enals, cyclic enones and allylic ketones with the aid of amine catalysts have found widespread applications in some highly appealing α-selective functionalizations and, far more intriguing, γ-selective functionalizations in recent times. Intramolecular Baylis–Hillman type reactions, asymmetric aza-Morita–Baylis–Hillman type products, chiral Michael adducts from addition to nitroolefins, intramolecular Rauhut–Currier cyclizations for the construction of chiral cyclopentenals, the asymmetric synthesis of cyclopentyl[b]indolines via the SN1 alkylation reaction of γ,γ-disubstituted α,β-unsaturated aldehydes with 3-indolylmethanols and the asymmetric benzoyloxylation of α-branched enals were attainable as α-selective functionalization. The category of γ-selective functionalization encompassed the asymmetric amination of α,β-unsaturated aldehydes, the synthesis of a key intermediate for α-tocopherol, aldol reactions with aldehydes, isatins (for the enantioselective synthesis of 3-substituted 3-hydroxyoxindole derivatives) and α-ketoesters (involving hydrogen-bond-directing dienamine catalysis), alkylation of α-branched enals, and the enantioselective Michael addition of cyclic enones to nitroalkenes and allyl alkyl ketones to maleimides. Moreover, γ-propargylation, γ-oxyamination and asymmetric γ-allylation of α,β-unsaturated aldehydes were achieved by combined dienamine and transition-metal catalysis. Enantioselective γ-alkylation of enals was also driven by the direct photoexcitation of dienamine intermediates. Further, γ-selective nitrone formation from an enal via a redox reaction is highlighted in this chapter.

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Recent Uses of Photogenerated Oxygen-Centered Radicals in Intermolecular C–O Bond Formation

Banoun

Magnier

Dagousset

2023

Synlett

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Organocatalytic γ-oxidation of α,β-unsaturated aldehydes

Cited by 3 publications

References 22 publications

Highly selective γ-alkoxylation, γ-amination and γ-alkylation of unbiased enals by means of photoredox catalysis

Highly selective γ-alkoxylation, γ-amination and γ-alkylation of unbiased enals by means of photoredox catalysis

Asymmetric α-Selective and Remote γ-Selective Functionalization of Enals and Enones Through Serebryakov–Jørgensen Dienamines (1-Aminobuta-1,3-Dienes)

Recent Uses of Photogenerated Oxygen-Centered Radicals in Intermolecular C–O Bond Formation

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