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Updated: Jun 30, 2026
08:46
Preparation and Reactivity of a Triphosphenium Bromide Salt: A Convenient and Stable Source of Phosphorus(I)
Published on: November 22, 2016
Dynamic resolution of N-Boc-2-lithiopiperidine
Iain Coldham1, Sophie Raimbault, Praful T Chovatia
1Department of Chemistry, University of Sheffield, Sheffield, UKS3 7HF. i.coldham@sheffield.ac.uk
Chemical Communications (Cambridge, England)
|September 20, 2008
Summary
Chiral ligands enable dynamic thermodynamic resolution of N-Boc-2-lithiopiperidine. This method successfully separates the organolithium
Area of Science:
- Organic Chemistry
- Stereochemistry
- Asymmetric Synthesis
Background:
- Organolithium compounds are crucial synthetic intermediates.
- Chiral resolution is essential for producing enantiomerically pure compounds.
- N-Boc-2-lithiopiperidine is a valuable chiral building block.
Purpose of the Study:
- To develop a method for the dynamic thermodynamic resolution of N-Boc-2-lithiopiperidine.
- To identify effective chiral ligands for this resolution process.
Main Methods:
- Screening of 26 chiral diamino-alkoxide ligands.
- Application of dynamic thermodynamic resolution principles.
- Analysis of enantiomeric excess and selectivity.
Main Results:
- Successful dynamic thermodynamic resolution of N-Boc-2-lithiopiperidine was achieved.
- High selectivities of up to 85:15 were obtained with specific chiral ligands.
- Identification of optimal chiral diamino-alkoxide ligands for the resolution.
Conclusions:
- Dynamic thermodynamic resolution is a viable strategy for N-Boc-2-lithiopiperidine.
- Chiral diamino-alkoxide ligands are effective in achieving high enantioselectivity.
- This method provides access to enantiomerically enriched N-Boc-2-lithiopiperidine.
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