2,6-Bis[(3aR,8aS)-(+)-8H-indeno[1,2-d]oxazolin-2-yl)pyridine
2,6-Bis[(3aR,8aS)-(+)-8H-indeno[1,2-d]oxazolin-2-yl)pyridine (CAS: 357209-32-6) is a chiral ligand with the molecular formula C25H19N3O2 and a molecular weight of 393.44 g/mol. This compound is primarily employed as a catalytic ligand in various asymmetric synthesis reactions, facilitating the stereoselective formation of complex organic molecules. Its defined stereochemistry is crucial for its efficacy in enantioselective transformations.
- IUPAC
- (3aR,3′aR,8aS,8′aS)-2,2′-(2,6-Pyridinediyl)bis[3a,8a-dihydro-8H-indeno[1,2-d]oxazole,(3aR,8aS)-in-pybox
- Synonyms
- 2-d]oxazolin-2-yl)pyridine357209-32-6C25H19N3O2(3aR,3′aR,8aS,8′aS)-2,2′-(2,6-Pyridinediyl)bis[3a,8a-dihydro-8H-indeno[1,2-d]oxazole(3aR,8aS)-in-pybox
![2,6-Bis[(3aR,8aS)-(+)-8H-indeno[1,2-d]oxazolin-2-yl)pyridine (C25H19N3O2) — chemical structure, CAS 357209-32-6; Chemistry, fine chemical supplied by Tech Serve Solutions](/_next/image?url=https%3A%2F%2Fpub-f4d920c906024441a773a96f7098e551.r2.dev%2Fimages%2Fproducts%2F357209-32-6.png&w=3840&q=75)
Enantioselective Cycloaddition and Aldol Reactions
This pybox ligand is instrumental in catalysing [3+2] cycloadditions of N-tosyl aziridines with electron-rich alkenes, enabling selective carbon-carbon bond cleavage. It also plays a key role in enantioselective Mukaiyama-aldol reactions.
Asymmetric Carbonyl-Ene and Alkynylation Reactions
The compound serves as a crucial ligand in enantioselective carbonyl-ene reactions. Furthermore, it is utilized in Cu(I)-catalyzed asymmetric alkynylation of imino esters with terminal alkynes, providing stereocontrolled access to alkynylated products.
Multicomponent and Coupling Reactions
A Cu/pybox complex formed with this ligand catalyses asymmetric three-component coupling reactions. It also finds application in Ni-catalyzed cross-coupling reactions, highlighting its versatility in complex bond formations.
Enantioselective Diels-Alder Reactions
This chiral ligand is effective in promoting enantioselective Diels-Alder reactions, a fundamental tool for constructing cyclic systems with high stereochemical control.
| Molecular weight | 393.44 |
|---|---|
| Empirical formula | C25H19N3O2 |
| Assay | ≥94% |
| Optical activity | [α]20/D +386°, c = 1 in methylene chloride(lit.) |
| Application | Catalytic ligand used for:• [3+2] cycloaddition of N-tosyl aziridines with electron-rich alkenes via selective carbon-carbon bond cleavage1• Enantioselective Mukaiyama-aldol reactions2• Enantioselective carbonyl-ene reactions3• Cu(I)-catalyzed asymmetric alkynylation of imino esters with terminal alkynes4• Asymmetric three-component coupling reactions catalyzed by a Cu/pybox complex5• Enantioselective Diels-Alder reaction6• Ni-catalyzed cross-coupling reactions7 |
| Melting point | 284 °C (dec.) |
Hazard statements
- H413May cause long-lasting harmful effects to aquatic life
| Water hazard class (WGK, DE) | 3 |
|---|
Hazard information is provided for guidance. Always consult the product Safety Data Sheet (SDS), available on request, before handling.
Documentation
Every batch ships with a Certificate of Analysis covering assay, identity and purity; the grade is confirmed against your enquiry. Safety Data Sheets and technical data sheets are available on request.
Supply & logistics
Samples for technical evaluation; bulk MOQ by grade and packaging. In-stock material ships in 7–10 working days, worldwide, with full export documentation.
What is 2,6-Bis[(3aR,8aS)-(+)-8H-indeno[1,2-d]oxazolin-2-yl)pyridine used for?
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This compound is used as a chiral ligand in various asymmetric synthesis applications, including cycloaddition, aldol, carbonyl-ene, alkynylation, and Diels-Alder reactions, as well as multicomponent and cross-coupling reactions.
What are the CAS number and formula for this product?
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The CAS number is 357209-32-6 and the empirical formula (Hill notation) is C25H19N3O2.
What grade and purity does Tech Serve Solutions supply?
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Tech Serve Solutions supplies this chemical with an assay of ≥94%. We do not represent this product as meeting USP, BP, EP, or other pharmacopoeia standards.
What are the safety and handling considerations?
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This compound may cause long lasting harmful effects to aquatic life (H413). It has a melting point of 284 °C (dec.). Handle with appropriate personal protective equipment in a well-ventilated area.
Is this product packed and shipped internationally?
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Yes, Tech Serve Solutions is a specialist global supplier and exporter of fine chemicals and laboratory reagents.
How can I request a sample or obtain a quote?
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Please contact our sales team directly to request a sample or to obtain a quotation for this product.
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