Enantioselective Synthesis of 2-Substituted Pyrrolidines from 4-Hydroxynitriles. Application to the Synthesis of the Dopamine Agonist rs-59022

doi:10.1080/00397919508012679

Paper

Enantioselective Synthesis of 2-Substituted Pyrrolidines from 4-Hydroxynitriles. Application to the Synthesis of the Dopamine Agonist rs-59022

Published Apr 1, 1995 · O. W. Gooding, Rekha Bansal

Synthetic Communications

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Abstract

Abstract Two novel routes to optically active 4-hydroxynitriles and the subsequent cyclization to 2-substituted pyrrolidines are described. The methodology is applied to the synthesis of the key intermediate used in the synthesis of the dopamine agonist RS-59022. Unusual selectivity in the CBS reduction of 4-oxonitriles is explained through structural and mechanistic analysis.

Study Snapshot

This study presents two novel routes to optically active 4-hydroxynitriles and their application in the synthesis of 2-substituted pyrrolidines, which are crucial for the dopamine agonist RS-59022.

PopulationOlder adults (50-71 years)

Sample size24

MethodsObservational

OutcomesBody Mass Index projections

ResultsSocial networks mitigate obesity in older groups.

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Paper

Enantioselective Synthesis of 2-Substituted Pyrrolidines from 4-Hydroxynitriles. Application to the Synthesis of the Dopamine Agonist rs-59022

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References

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Oxazaborolidine-catalyzed reduction of trihalomethyl ketones by catecholborane exhibits high enantioselectivity due to structural and mechanistic analyses.

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This efficient asymmetric synthesis of 2-substituted pyrrolidines and 5-substituted pyrrolidinones in high enantiomeric purity has been realized starting from 3-acylpropionic acids.

Bakers' Yeast Reduction of γ and δ Ketonitriles: Intermediates for the Synthesis of (S)-5-Hexanolide and Other Chiral Lactones

Bakers' yeast effectively reduces and ketonitriles to useful intermediates for the synthesis of chiral lactones, including (S)()-4-methylbutyrolactone and (S)-()-5-hexanolide.

Macromodel—an integrated software system for modeling organic and bioorganic molecules using molecular mechanics

Macromodel is a user-friendly, atom-based system for modeling organic and bioorganic molecules using molecular mechanics, allowing for the construction, display, and manipulation of complex structures with up to 10,000 atoms.

Citations

Formal synthesis of berkelic acid: a lesson in α-alkylation chemistry.

The enantioselective formal synthesis of berkelic acid was achieved using a silyl enol ether and a one-pot debenzylation/spiroketalisation/thermodynamic equilibration procedure.

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This enantioselective formal synthesis of berkelic acid enables the construction of the tetracyclic core as a single diastereoisomer, with a key step involving silyl enol ether addition to benzannulated ox

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This new method allows for the rapid and general synthesis of 2-substituted pyrrolidines from commercially available starting materials in three steps, with high yields and good diastereoselectivities.

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Chiral 1,3,2-oxazaborolidines are effective in enantioselective reduction of ketones, imines, and oxime ethers, asymmetric Diels-Alder reactions, aldol condensation, and atroposelective reduction of lactones.

N‐Methylmorpholine Polystyrene

N-methylmorpholine polystyrene is a polymer-supported tertiary amine base used as an acid scavenger in various solvents.