Development of a one-pot asymmetric azaelectrocyclization protocol: synthesis of chiral 2,4-disubstituted 1,2,5,6-tetrahydropyridines.

doi:10.1021/OL061405C

Paper

Development of a one-pot asymmetric azaelectrocyclization protocol: synthesis of chiral 2,4-disubstituted 1,2,5,6-tetrahydropyridines.

Published Jul 21, 2006 · Toyoharu Kobayashi, Miyuki Nakashima, T. Hakogi

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51

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Abstract

[reaction: see text] A one-pot procedure for tetracyclic chiral aminoacetals, the useful precursors for substituted piperidine synthesis, has been established via Stille-Migita coupling, 6pi-azaelectrocyclization, and aminoacetal formation from readily prepared vinylstannanes, vinyliodides, and cis-aminoindanol derivatives. Based on the method, chiral 2,4-disubstituted 1,2,5,6-tetrahydropyridines, bearing a variety of aromatic substituents at the C-2 position, have been prepared.

Study Snapshot

This one-pot method allows for the synthesis of chiral 2,4-disubstituted 1,2,5,6-tetrahydropyridines with various aromatic substituents, making it a useful precursor for substituted piperidine synthesis.

PopulationOlder adults (50-71 years)

Sample size24

MethodsObservational

OutcomesBody Mass Index projections

ResultsSocial networks mitigate obesity in older groups.

Paper

Development of a one-pot asymmetric azaelectrocyclization protocol: synthesis of chiral 2,4-disubstituted 1,2,5,6-tetrahydropyridines.

References

Development of highly stereoselective asymmetric 6pi-azaelectrocyclization of conformationally flexible linear 1-azatrienes. from determination of multifunctional chiral amines, 7-alkyl cis-1-amino-2-indanols, to application as a new synthetic strategy: formal synthesis of 20-epiuleine.

This study developed a highly stereoselective asymmetric 6pi-azaelectrocyclization method, successfully applied to the formal synthesis of optically active 20-epiuleine, using conformationally flexible linear 1-azatrienes and effective chiral amines.

Synthesis of new chiral auxiliaries for 6π-azaelectrocyclization: 4- and 7-alkyl substituted cis-1-amino-2-indanols

New chiral auxiliaries, 7-alkyl substituted cis-1-amino-2-indanol derivatives, effectively serve as nitrogen sources in asymmetric 6-azaelectrocyclization.

Highly enantioenriched tetrahydropyridines from chiral organosilanes: application to the synthesis of quinolizidine alkaloid (-)-217A.

This study presents a novel method for preparing enantioenriched tetrahydropyridines with high diastereoselectivity, enabling the rapid total synthesis of (-)-quinolizidine 217A.

Highly stereoselective asymmetric 6pi-azaelectrocyclization utilizing the novel 7-alkyl substituted cis-1-amino-2-indanols: formal synthesis of 20-epiuleine.

This study successfully synthesized 20-epiuleine using a novel method for highly stereoselective asymmetric 6pi-azaelectrocyclization using novel chiral amines and manganese dioxide oxidation under mild conditions.

Significant acceleration of 6 pi-azaelectrocyclization resulting from a remarkable substituent effect and formal synthesis of the ocular age pigment A2-E by a new method for substituted pyridine synthesis.

This study demonstrates a significant acceleration of 6 pi-azaelectrocyclization and the formal synthesis of the ocular age pigment A2-E using a new method for substituted pyridine synthesis.

Citations