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Abstract
The ring opening of NH-aziridines with thiols was found to proceed in good yield at room temperature in the presence of an ionic liquid1-butyl-3-methylimidazolium chloride (BMIM chloride). This mild methodology was applied to the synthesis of a camphor-derived chiral aminosulfide. The sulfide was used to generate a sulfur ylide, which effected an asymmetric epoxidation of benzaldehyde (e.r. 85:15, trans:cis 90:10, 87% yield). The amino group enabled easy recovery of the sulfide (98% yield) after the reaction by a simple acid/base extraction.
Original language | English |
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Article number | 922590300 |
Pages (from-to) | 1250-1272 |
Number of pages | 23 |
Journal | Phosphorus, Sulfur, and Silicon and the Related Elements |
Volume | 185 |
Issue number | 5-6 |
DOIs | |
Publication status | Published - 2010 |
Keywords
- Aziridine ring-opening
- asymmetric epoxidation
- ionic liquids
- sulfide
- sulfur ylide
- thiols
- YLIDE-MEDIATED EPOXIDATION
- DIELS-ALDER REACTION
- ENANTIOSELECTIVE SYNTHESIS
- TRANSFER HYDROGENATION
- CARBONYL-COMPOUNDS
- CHIRAL AUXILIARY
- SULFUR YLIDES
- EPOXIDES
- DERIVATIVES
- REDUCTION
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Dive into the research topics of 'Ring-Opening of NH-Aziridines with Thiols in Ionic Liquids: Application to the Synthesis of Aminosulfide Catalysts for Asymmetric Epoxidation of Aldehydes'. Together they form a unique fingerprint.Projects
- 1 Finished
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NEW ASSYMETRIC REACTIONS AND THEIR APPLICATION IN TOTAL SYNTHESIS
Aggarwal, V. K. (Principal Investigator)
1/10/05 → 1/10/10
Project: Research