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798363 Sigma-Aldrich

Endo-Phenyl Kwon [2.2.1] Bicyclic Phosphine

95% (HPLC)

Synonym: (1S,4S,5S)-5-(phenyl)-2-tosyl-2-aza-5-phosphabicyclo[2.2.1]heptane

  • Empirical Formula (Hill Notation) C18H20NO2PS

  • Molecular Weight 345.40

  •  MDL number MFCD28016350

  •  PubChem Substance ID 329768643

  •  NACRES NA.22

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Properties

Related Categories Asymmetric Synthesis, Chemical Synthesis, Chiral Catalysts, Ligands, and Reagents, Kwon Chiral Phosphines
Quality Level   100
assay   95% (HPLC)
form   powder
storage condition   under inert gas
mp   96-101 °C
storage temp.   2-8°C
SMILES string   O=S(N1C[C@@]2([H])[P@@](C3=CC=CC=C3)C[C@]1([H])C2)(C4=CC=C(C)C=C4)=O
InChI   1S/C18H20NO2PS/c1-14-7-9-18(10-8-14)23(20,21)19-12-17-11-15(19)13-22(17)16-5-3-2-4-6-16/h2-10,15,17H,11-13H2,1H3/t15-,17-,22?/m0/s1
InChI key   BWXYDSDVFPJTFY-TWMUNHRGSA-N

Description

Application

The bicyclic, chiral phosphine was developed by the Kwon Research Group.Its initial applications were for asymmetric [3+2] annulation between allenes and imines as well as the first examples of phosphine-catalyzed asymmetric syntheses of 1,2,3,5-substituted pyrrolines. Along with nucleophilic organocatalysis, the P-chiral phosphines may also find utility in asymmetric transition-metal catalysis.

Packaging

100 mg in clear glass bottle

Other Notes

Hydroxyproline-Derived Pseudoenantiomeric [2.2.1] Bicyclic Phosphines: Asymmetric Synthesis of (+)- and (-)-Pyrrolines

Technology Spotlight- Kwon Phosphines: P-Chiral Monodentate Phosphines from Hydroxyproline

Aldrichimica Acta Review- Nucleophilic Chiral Phosphines: Powerful and Versatile Catalysts for Asymmetric Annulations

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

Kwon Phosphines: P-Chiral Monodentate Phosphines from Hydroxyproline

Chiral phosphines have been the staple ligands for asymmetric transition metal catalysis and more recently operate as catalysts in organic phosphinocatalysis. Chiral phosphines that possess a stereog...
Keywords: Addition reactions, Aerobic, Annulations, Asymmetric synthesis, Catalysis, Cycloadditions, Ligands, Oxidations

Ohyun Kwon Group – Professor Product Portal

From our library of Articles, Sigma-Aldrich presents Ohyun Kwon Group – Professor Product Portal
Keywords: Addition reactions, Annulations, Asymmetric synthesis, Capillary electrophoresis, Catalysis, Coupling reactions, Cross couplings, Organocatalysis, Transmetalation

Peer-Reviewed Papers
15

References

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