Studies on pyrrolidinones. On the decarboxylation of pyroglutamic acids and N-acyl prolines in acidic media

Akué‐Gédu, Rufine; Ebrik, Sahar Al Akoum; Witczak‐Legrand, Anne; Fasseur, D.; Ghammarti, Samira El; Couturier, Daniel; Decroix, Bernard; Othman, Mohamed Rozali; DeBacker, Marc G.; Rigo, Benoı̂t

doi:10.1016/s0040-4020(02)01183-3

Cited by 18 publications

(1 citation statement)

References 30 publications

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“…Formation of 4 from 2d can be explained by a prior E1-type elimination reaction followed by a double bond isomerization (Scheme ) . We conjecture that the formation of 4 from N - acyliminium ion is reversible and also much faster compared to the substitution step (S N 1-type) which leads to the alkylated product 3 .…”

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confidence: 90%

A Multimetallic Piano-Stool Ir–Sn₃ Catalyst for Nucleophilic Substitution Reaction of γ-Hydroxy Lactams through N-Acyliminium Ions

Maity

Roy

2012

J. Org. Chem.

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A multimetallic piano-stool complex [Cp*Ir(SnCl(3))(2){SnCl(2)(H(2)O)(2)}] (1) having Ir-Sn(3) motif has been synthesized from [Cp*IrCl(2)](2) and SnCl(2). The multimetallic complex catalytically promotes the nucleophilic substitution reaction (here after α-amidoalkylation reaction) of γ-hydroxylactams generated from phthalimidals to obtain decorated isoindolinones in excellent yields. Succinamidals, however, lead to the substituted pyrrolidinones (thermodynamic control product) via S(N)1-type path as well as eliminated pyrrolinones (kinetic control product) via an E1-type path, depending on the reaction parameters. A straightforward application of this methodology is to synthesize benzo-fused indolizidine alkaloid mimics.

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confidence: 90%

A Multimetallic Piano-Stool Ir–Sn₃ Catalyst for Nucleophilic Substitution Reaction of γ-Hydroxy Lactams through N-Acyliminium Ions

Maity

Roy

2012

J. Org. Chem.

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The Reactivity of Enantiopure (S)‐6‐Oxopipecolic Acid and Corresponding Pyridoisoquinolines Under Acidic Conditions

et al. 2018

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Enantiopure N‐benzyl 6‐oxopipecolic acid, obtained from (S)‐2‐aminoadipic acid, was evaluated under π‐cationic cyclization conditions. If the combination of SOCl2/AlCl3 seems to be superior in terms of the reaction yields, use of PPA, (CF3CO)2O/BF3·Et2O, and Eaton's reagent is also very interesting since in addition to the expected keto‐lactam, reduced‐ and oxidized keto‐lactam, enamides and enamidones containing CF3CO– residue are isolated. Mechanisms leading to these products as well as the ones resulting from their acidic treatment were proposed and discussed with the help, in some cases, of univocal transformations and X‐ray analysis.

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Studies on pyrrolidones. An improved synthesis of N‐arylmethyl pyroglutamic acids

Bourry

Akué‐Gédu

Rigo

et al. 2003

Journal of Heterocyclic Chem

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Low solubility of the aromatic aldehyde in a water/ethanol medium can prevent the sodium borohydride reductive alkylation of the sodium salt of glutamic acid. In that case, the reductive alkylation can be realized in methanol by using a triethylammonium salt. The uses of 2 molar equivalent of triethylammonium salt of glutamic acid for one molar equivalent of aldehyde strongly raise the yields. Cyclization of the N‐substituted glutamic acids obtained gives then N‐arylmethyl pyroglutamic acids in good yields.

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Studies on pyrrolidinones. On the decarboxylation of pyroglutamic acids and N-acyl prolines in acidic media

Cited by 18 publications

References 30 publications

A Multimetallic Piano-Stool Ir–Sn₃ Catalyst for Nucleophilic Substitution Reaction of γ-Hydroxy Lactams through N-Acyliminium Ions

A Multimetallic Piano-Stool Ir–Sn₃ Catalyst for Nucleophilic Substitution Reaction of γ-Hydroxy Lactams through N-Acyliminium Ions

The Reactivity of Enantiopure (S)‐6‐Oxopipecolic Acid and Corresponding Pyridoisoquinolines Under Acidic Conditions

Studies on pyrrolidones. An improved synthesis of N‐arylmethyl pyroglutamic acids

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Studies on pyrrolidinones. On the decarboxylation of pyroglutamic acids and N-acyl prolines in acidic media

Cited by 18 publications

References 30 publications

A Multimetallic Piano-Stool Ir–Sn3 Catalyst for Nucleophilic Substitution Reaction of γ-Hydroxy Lactams through N-Acyliminium Ions

A Multimetallic Piano-Stool Ir–Sn3 Catalyst for Nucleophilic Substitution Reaction of γ-Hydroxy Lactams through N-Acyliminium Ions

The Reactivity of Enantiopure (S)‐6‐Oxopipecolic Acid and Corresponding Pyridoisoquinolines Under Acidic Conditions

Studies on pyrrolidones. An improved synthesis of N‐arylmethyl pyroglutamic acids

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Product

Resources

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A Multimetallic Piano-Stool Ir–Sn₃ Catalyst for Nucleophilic Substitution Reaction of γ-Hydroxy Lactams through N-Acyliminium Ions

A Multimetallic Piano-Stool Ir–Sn₃ Catalyst for Nucleophilic Substitution Reaction of γ-Hydroxy Lactams through N-Acyliminium Ions