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804568 Sigma-Aldrich

(R,S)-Bode Kinetic Resolution Catalyst

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

  • CAS Number 1394957-71-1

  • Empirical Formula (Hill Notation) C11H10BrNO3

  • Molecular Weight 284.11

  •  PubChem Substance ID 329768882

  •  NACRES NA.22

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Properties

Related Categories Asymmetric Synthesis, Chemical Synthesis, Chiral Catalysts, Ligands, and Reagents, Other Organocatalysts
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+/m0/s1
InChI key   FQXSUQCCAHKURK-GXSJLCMTSA-N

Description

Application

The following hydroxamic acid catalyst was shown by Bode and coworkers to assist in the kinetic resolution of cyclic amines through acylation of one enantiomer, which can be controlled using either the (R or S)- or (S or R)-Bode Kinetic Resolution Catalyst, both of which are also available through Sigma-Aldrich.
It can also be employed in the preparation of nonracemic piperidines by kinetic resolution using an α-hydroxy-α′, β-unsaturated ketone in the presence of a pyrrolotriazolium salt.

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

Peer-Reviewed Papers
15

References

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