Stereoselective synthesis of 3-hydroxyproline benzyl esters from N-protected beta-aminoaldehydes and benzyl diazoacetate.

doi:10.1021/JO030360F

Paper

Stereoselective synthesis of 3-hydroxyproline benzyl esters from N-protected beta-aminoaldehydes and benzyl diazoacetate.

Published May 20, 2004 · S. R. Angle, Dominique S. Belanger

The Journal of organic chemistry

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Abstract

The synthesis of a series of 3-hydroxyproline benzyl esters from alpha-alkyl and alpha-alkoxy N-protected aminoaldehydes with benzyl diazoacetate is described. Aldehydes with alpha-alkyl substituents afforded prolines as a single diastereomer with a trans-cis relative configuration in 14-77%. An alpha-tert-butyldimethylsilyloxy aminoaldehyde afforded a proline as a single diastereomer with a trans-trans relative configuration in 37% yield.

Study Snapshot

This study demonstrates a stereoselective synthesis of 3-hydroxyproline benzyl esters from N-protected beta-aminoaldehydes and benzyl diazoacetate, yielding prolines with trans-cis and trans-trans configurations, respectively.

PopulationOlder adults (50-71 years)

Sample size24

MethodsObservational

OutcomesBody Mass Index projections

ResultsSocial networks mitigate obesity in older groups.

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Paper

Stereoselective synthesis of 3-hydroxyproline benzyl esters from N-protected beta-aminoaldehydes and benzyl diazoacetate.

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References

Citations

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The X-H insertion/cyclization cascade is a step-economical approach for constructing diverse heterocyclic systems, particularly in asymmetric synthesis.

C-H and C-C bond insertion reactions of diazo compounds into aldehydes

Diaz compounds can be efficiently inserted into aldehydes for the formation of ketones and homologated aldehydes, with applications in organic synthesis and natural product syntheses.

Synthesis of Nitrogen-Containing Heterocycles and Cyclopentenone Derivatives via Phosphine-Catalyzed Michael Addition/Intramolecular Wittig Reaction

The phosphine-catalyzed Michael addition/intramolecular Wittig reaction enables rapid access to nitrogen-containing heterocycles and cyclopentenone derivatives in good yields, with potential applications in natural products and bioactive compounds.

Boron trifluoride etherate

Boron trifluoride etherate is a versatile catalyst for various chemical reactions, including synthesis of cyclopentenones, cyclopentenone annelation, and cyclization of humulene-4,5-epoxide.

Silicon-Containing Amino Acids: Synthetic Aspects, Conformational Studies, and Applications to Bioactive Peptides.

Silicon-containing amino acids show promise for maintaining biological activity and resistance to enzyme degradation in bioactive peptides, with potential for future pharmaceutical innovations.