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CAS RN: 903571-02-8 | Product Number: D3983

(+)-(5aR,10bS)-5a,10b-Dihydro-2-(2,4,6-trimethylphenyl)-4H,6H-indeno[2,1-b][1,2,4]triazolo[4,3-d][1,4]oxazinium Chloride Monohydrate


Purity: >98.0%(HPLC)
Synonyms:
  • (+)-(5aR,10bS)-5a,10b-Dihydro-2-mesityl-4H,6H-indeno[2,1-b][1,2,4]triazolo[4,3-d][1,4]oxazinium Chloride Monohydrate
  • Bode Catalyst 2 Monohydrate
Documents:
100MG
€191.00
5   ≥20 

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Product Number D3983
Purity / Analysis Method >98.0%(HPLC)
Molecular Formula / Molecular Weight C__2__1H__2__2ClN__3O·H__2O = 385.9  
Physical State (20 deg.C) Solid
CAS RN 903571-02-8
Reaxys Registry Number 10505362
PubChem Substance ID 125307585
MDL Number

MFCD10566989

Specifications
Appearance White to Gray to Red powder to crystal
Purity(HPLC) min. 98.0 area%
Elemental analysis(Nitrogen) 10.40 to 11.20 %
Specific rotation [a]20/D +155 to +163 deg(C=1, CHCl3)
Properties (reference)
Melting Point 219 °C
Specific Rotation 158° (C=1,CHCl3)
GHS
Related Laws: / Compliance with laws, Regulations
Transport Information:
HS Number 2934999090
Application
Highly Enantioselective Diels-Alder Reactions using Bode 2 Catalyst

References

1)M. He, J. R. Struble, J. W. Bode, J. Am. Chem. Soc. 2006, 128, 8418.

2)M. He, G. J. Uc, J. W. Bode, J. Am. Chem. Soc. 2006, 128, 15088.

3)J. R. Struble, J. W. Bode, Y. Lian, H. M. L. Davies, Org. Synth. 2010, 87, 362


Application
[4+2] Cycloaddition of α,β-Unsaturated Aldehydes with Chalcones Using NHC (Bode Catalyst 2) and Acid Co-catalyst

Typical procedure (entry 1):
A dry 10 mL Schlenk tube is successively charged with 4-methoxycinnamaldehyde (81 mg, 0.5 mmol), chalcone (52 mg, 0.25 mmol), Bode catalyst 2 monohydrate (18.4 mg, 0.05 mmol), KOAc (61.4 mg, 0.625 mmol) and MS4Å (100 mg). The tube is closed with a septum, evacuated, and refilled with nitrogen. To this mixture is added distilled THF (0.5 mL), followed by AcOH (7.2 µL, 0.0625 mmol). The reaction mixture is stirred at room temperature for 24 h. After the reaction is completed, the solvent is removed under reduced pressure. The residue is purified by column chromatography on silica gel (eluent: hexane/ethyl acetate = 10/1) to afford the corresponding lactone (79.6 mg, 86% yield, 20:1 dr, 99% ee) as a white solid.

References


PubMed Literature


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