3.17 The Favorskii Rearrangement (Extend to Rings)

Butkus, Eugenijus

doi:10.1016/b978-0-08-097742-3.00323-2

Comprehensive Organic Synthesis II 2014

DOI: 10.1016/b978-0-08-097742-3.00323-2

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3.17 The Favorskii Rearrangement (Extend to Rings)

Eugenijus Butkus

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Cited by 5 publications

(1 citation statement)

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“…In particular, the ring-contraction reaction involving the migration of carbonyl group is an attractive and useful reaction due to the further introduction of a nucleophile to the migrated carbonyl group. This reaction proceeds via the rearrangement of several C–C bonds, and representative examples include the pinacol rearrangement, Wolff rearrangement, Favorskii rearrangement, and benzylic acid rearrangement . Therefore, these ring contraction strategies are applied for the synthesis of biologically active and natural products .…”

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Sequential Nucleophilic Arylation/Ring-Contractive Rearrangement of N-Alkoxylactams

et al. 2020

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A nucleophilic addition/ring-contractive rearrangement of α-bromo N-alkoxylactams with organometallic reagents was developed, providing an efficient access to α-acylpyrrolidines incorporating various C(sp 2) units such as aryl, heteroaryl, and alkenyl groups. The sequential reaction proceeds through a five-membered chelate formation using nucleophilic addition followed by ring contraction via the formation of N,O-hemiaminal with good yields and a broad substrate scope. Moreover, a preliminary result with the use of the chiral N-alkoxylactam for the diastereoselective reaction is described.

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Sequential Nucleophilic Arylation/Ring-Contractive Rearrangement of N-Alkoxylactams

et al. 2020

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Strain‐Induced Nucleophilic Ring Opening of Donor–Acceptor Cyclopropenes for Synthesis of Monosubstituted Succinic Acid Derivatives

Marichev

Wang

Greco

et al. 2020

Chemistry A European J

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1,2,3-Trisubstituted donor-acceptor cyclopropenes (DACPs) generatedi ns itu from enoldiazo compounds react with nucleophilest of orm a-substituted succinic acid derivatives in high yields. Initial dirhodium(II)c arboxylate catalysis rapidly converts enoldiazo-acetates or-acetamides to DACPs that undergo catalyst-free Favorskii ring openingw ith amines, and also with anilines,a lcohols, and thiols, when facilitated by catalytic amounts of 4-dimethylaminopyridine (DMAP). This methodology providese asy access to mixed esters and amides of monosubstituted succinic acids, including derivatives of naturallyo ccurring compounds.I ta lso affords dihydrazide, dihydroxamic acid, and diamide derivatives, as well as a-substituted tetrahydropyridazine-3,6diones in high yields. Attempts to generate optically enriched DACPs were not successful because their populations having the R and S configurations formedw ithachiral dirhodiumcatalystare quite similar, and the loss of enantiocontrol likely originates from the DACP ring forming step which is reversible with its intermediate metal carbene. Scheme1.Nucleophilic retro-Claisen and Favorskii-type ring opening of strained ring systems.

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Cyclization Reactions of Oxyallyl Cation. A Method for Cyclopentane Ring Formation

et al. 2019

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3.17 The Favorskii Rearrangement (Extend to Rings)

Cited by 5 publications

References 111 publications

Sequential Nucleophilic Arylation/Ring-Contractive Rearrangement of N-Alkoxylactams

Sequential Nucleophilic Arylation/Ring-Contractive Rearrangement of N-Alkoxylactams

Strain‐Induced Nucleophilic Ring Opening of Donor–Acceptor Cyclopropenes for Synthesis of Monosubstituted Succinic Acid Derivatives

Cyclization Reactions of Oxyallyl Cation. A Method for Cyclopentane Ring Formation

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