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804584 Sigma-Aldrich

(S,R)-Bode Kinetic Resolution Catalyst

Synonym: (4aS,9aR)-6-Bromo-4-hydroxy-4,4a,9,9a-tetrahydroindeno[2,1-b][1,4]oxazin-3(2H)-one

  • CAS Number 1417826-81-3

  • Empirical Formula (Hill Notation) C11H10BrNO3

  • Molecular Weight 284.11

  •  PubChem Substance ID 329768884

  •  NACRES NA.22

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Properties

Quality Level   100
SMILES string   O=C(CO1)N(O)[C@]2([H])[C@@]1([H])CC3=CC=C(Br)C=C32
InChI   1S/C11H10BrNO3/c12-7-2-1-6-3-9-11(8(6)4-7)13(15)10(14)5-16-9/h1-2,4,9,11,15H,3,5H2/t9-,11+/m1/s1
InChI key   FQXSUQCCAHKURK-KOLCDFICSA-N

Description

Application

The following organocatalyst is used in the kinetic resolution of cyclic amines as reported by Bode and coworkers. In tandem with acylating reagent, (1E)-4-Hydroxy-1-mesityl-4-methylpent-1-en-3-one, either enantiomer can be accessed by using the catalyst shown or its enantiomer, both of which are available from Sigma-Aldrich.

Packaging

100 mg in glass bottle

Other Notes

Expanded substrate scope and catalyst optimization for the catalytic kinetic resolution of N-heterocycles

Safety & Documentation

Safety Information

Symbol 
GHS07  GHS07
Signal word 
Warning
Hazard statements 
Precautionary statements 
RIDADR 
NONH for all modes of transport
WGK Germany 
WGK 3
Flash Point(F) 
Not applicable
Flash Point(C) 
Not applicable

Documents

Certificate of Analysis (COA)

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Certificate of Origin (COO)

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Protocols & Articles

Articles

Bode Kinetic Resolution

Despite the widespread use of chiral amines and amides in modern pharmaceutical and agrochemical compounds, synthetic access to such building blocks, particularly in an enantioenriched form, has trad...
Keywords: Agrochemicals, Amidations, Asymmetric synthesis, Building blocks, Catalysis, Chiral chromatography, Chromatography, Column chromatography, Pharmaceutical, Purification

Jeffrey Bode Group – Professor Product Portal

From our library of Articles, Sigma-Aldrich presents Jeffrey Bode Group – Professor Product Portal
Keywords: Annulations, Asymmetric synthesis, Catalysis, Cross couplings, transformation

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