Browse
Submit Data
Databases
API
Help

Dataset Information

16 Views

0 Connections

0 Citations

0 Reanalyses

0 Downloads

Omics score: 0

Decarboxylative Annulation of ?-Amino Acids with ?-Nitroaldehydes.

ABSTRACT: Indolizidine and quinolizidine derivatives are readily assembled from proline or pipecolic acid and ?-nitroaldehydes by means of a decarboxylative annulation process. These reactions are promoted by simple acetic acid and involve azomethine ylides as reactive intermediates. The method was applied to the synthesis of an epiquinamide analog.

SUBMITTER: Kang Y

PROVIDER: S-EPMC5013532 | biostudies-literature | 2016 Sep

REPOSITORIES: biostudies-literature

ACCESS DATA

Json Xml

Publications

Decarboxylative Annulation of α-Amino Acids with γ-Nitroaldehydes.

Kang YoungKu Y Seidel Daniel D

Organic letters 20160810 17

Indolizidine and quinolizidine derivatives are readily assembled from proline or pipecolic acid and γ-nitroaldehydes by means of a decarboxylative annulation process. These reactions are promoted by simple acetic acid and involve azomethine ylides as reactive intermediates. The method was applied to the synthesis of an epiquinamide analog. ...[more]

PMID: 27509449

Similar Datasets

Decarboxylative Annulation of ?-Amino Acids with ?-Ketoaldehydes.

Project description:Indolizidine and quinolizidine derivatives are readily assembled from l-proline or (±)-pipecolic acid and ?-ketoaldehydes via a decarboxylative annulation process. These reactions are promoted by acetic acid and involve azomethine ylides as reactive intermediates.

| S-EPMC5937137 | biostudies-literature

Dual Catalytic Decarboxylative Allylations of ?-Amino Acids and Their Divergent Mechanisms.

Project description:The room temperature radical decarboxylative allylation of N-protected ?-amino acids and esters has been accomplished via a combination of palladium and photoredox catalysis to provide homoallylic amines. Mechanistic investigations revealed that the stability of the ?-amino radical, which is formed by decarboxylation, dictates the predominant reaction pathway between competing mechanisms.

| S-EPMC4715668 | biostudies-literature

Decarboxylative allylation of amino alkanoic acids and esters via dual catalysis.

Project description:A combination of photoredox and palladium catalysis has been employed to facilitate the room temperature decarboxylative allylation of recalcitrant ?-amino and phenylacetic allyl esters. This operationally simple process produces CO2 as the only byproduct and provides direct access to allylated alkanes. After photochemical oxidation, the carboxylate undergoes radical decarboxylation to site-specifically generate radical intermediates which undergo allylation. A radical dual catalysis mechanism is proposed. Free phenylacetic acids were also allylated utilizing similar reactions conditions.

| S-EPMC4183636 | biostudies-literature

Enantioselective Decarboxylative Arylation of ?-Amino Acids via the Merger of Photoredox and Nickel Catalysis.

Project description:An asymmetric decarboxylative Csp(3)-Csp(2) cross-coupling has been achieved via the synergistic merger of photoredox and nickel catalysis. This mild, operationally simple protocol transforms a wide variety of naturally abundant ?-amino acids and readily available aryl halides into valuable chiral benzylic amines in high enantiomeric excess, thereby producing motifs found in pharmacologically active agents.

| S-EPMC4862596 | biostudies-literature

Decarboxylative Polyfluoroarylation of Alkylcarboxylic Acids.

Project description:Polyfluoroarenes are useful building blocks in several areas such as drug discovery, materials, and crop protection. Herein, we report the first polyfluoroarylation of aliphatic carboxylic acids via photoredox decarboxylation. The method proceeds with broad substrate scope and high functional group tolerance. Moreover, small complex molecules such as natural products and drugs can be modified by late-stage modification.

| S-EPMC8252513 | biostudies-literature

Decarboxylative Hydroxylation of Benzoic Acids.

Project description:Herein, we report the first decarboxylative hydroxylation to synthesize phenols from benzoic acids at 35 °C via photoinduced ligand-to-metal charge transfer (LMCT)-enabled radical decarboxylative carbometalation. The aromatic decarboxylative hydroxylation is synthetically promising due to its mild conditions, broad substrate scope, and late-stage applications.

| S-EPMC8596882 | biostudies-literature

Nickel-Catalyzed Oxidative Decarboxylative Annulation for the Synthesis of Heterocycle-Containing Phenanthridinones.

Project description:A nickel-catalyzed oxidative decarboxylative annulation reaction of simple benzamides and (hetero)aromatic carboxylates has been developed. This reaction provides access to a large array of phenanthridinones and their heterocyclic analogues, highlighting the utility and versatility of oxidative decarboxylative coupling strategies for C-C bond formation.

| S-EPMC6739634 | biostudies-literature

Hydrogen radical-shuttle (HRS)-enabled photoredox synthesis of indanones via decarboxylative annulation.

Project description:Hydrogen atom transfer (HAT) process is a powerful and effective strategy for activating C-H bonds followed by further functionalization. Intramolecular 1,n (n = 5 or 6)-HATs are common and frequently encountered in organic synthesis. However, intramolecular 1,n (n = 2 or 3)-HAT is very challenging due to slow kinetics. Compared to proton-shuttle process, which is well established for organic synthesis, hydrogen radical-shuttle (HRS) is unexplored. In this work, a HRS-enabled decarboxylative annulation of carbonyl compounds via photoredox catalysis for the synthesis of indanones is developed. This protocol features broad substrate scope, excellent functional group tolerance, internal hydrogen radical transfer, atom- and step-economy. Critical to the success of this process is the introduction of water, acting as both HRS and hydrogen source, which was demonstrated by mechanistic experiments and density functional theory (DFT) calculations. Importantly, this mechanistically distinctive HAT provides a complement to that of typical proton-shuttle-promoted, representing a breakthrough in hydrogen radical transfer, especially in the inherently challenging 1,2- or 1,3-HAT.

| S-EPMC8421331 | biostudies-literature

Decarboxylative Trifluoromethylation of Aliphatic Carboxylic Acids.

Project description:Herein we disclose an efficient method for the conversion of carboxylic acids to trifluoromethyl groups via the combination of photoredox and copper catalysis. This transformation tolerates a wide range of functionality including heterocycles, olefins, alcohols, and strained ring systems. To demonstrate the broad potential of this new methodology for late-stage functionalization, we successfully converted a diverse array of carboxylic acid-bearing natural products and medicinal agents to the corresponding trifluoromethyl analogues.

| S-EPMC6538506 | biostudies-literature

Enantioselective decarboxylative chlorination of ?-ketocarboxylic acids.

Project description:Stereoselective halogenation is a highly useful organic transformation for multistep syntheses because the resulting chiral organohalides can serve as precursors for various medicinally relevant derivatives. Even though decarboxylative halogenation of aliphatic carboxylic acids is a useful and fundamental synthetic method for the preparation of a variety of organohalides, an enantioselective version of this reaction has not been reported. Here we report a highly enantioselective decarboxylative chlorination of ?-ketocarboxylic acids to obtain ?-chloroketones under mild organocatalytic conditions. The present method is also applicable for the enantioselective synthesis of tertiary ?-chloroketones. The conversions of the resulting ?-chloroketones into ?-aminoketones and ?-thio-substituted ketones via SN2 reactions at the tertiary carbon centres are also demonstrated. These results constitute an efficient approach for the synthesis of chiral organohalides and are expected to enhance the availability of enantiomerically enriched chiral compounds with heteroatom-substituted chiral stereogenic centres.

| S-EPMC5465354 | biostudies-literature

OmicsDI is part of the ELIXIR infrastructure

OmicsDI is an Elixir interoperability service. Learn more ›

OmicsDI Databases

PRIDE
PeptideAtlas
MassIVE
JPOST Repository
Physiome Model Repository

EGA
EVA
ENA
LINCS
PAXDB
Cell Collective

MetaboLights
Metabolomics Workbench
MetabolomeExpress
GNPS
BioModels
FAIRDOMHub

ArrayExpress
dbGaP
ExpressionAtlas
GEO
NODE

Information

Databases
Help
API
Contact us
Code on GitHub
Terms of use
Submit Data