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798746 Sigma-Aldrich

Exo-4-anisole Kwon [2.2.1] bicyclic phosphine

Synonym: (1S,4S,5R)-5-(4-methoxyphenyl)-2-tosyl-2-aza-5-phosphabicyclo[2.2.1]heptane, Exo-4-Methoxyphenyl Kwon [2.2.1] Bicyclic Phosphine

  • Empirical Formula (Hill Notation) C19H22NO3PS

  • Molecular Weight 375.42

  •  MDL number MFCD28016352

  •  PubChem Substance ID 329768668

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Properties

Related Categories Asymmetric Synthesis, Chemical Synthesis, Chiral Catalysts, Ligands, and Reagents, Kwon Chiral Phosphines
Quality Level   100
form   powder
mp   85-90 °C
SMILES string   O=S(N1C[C@@]2([H])[P@](C3=CC=C(OC)C=C3)C[C@]1([H])C2)(C4=CC=C(C)C=C4)=O
InChI   1S/C19H22NO3PS/c1-14-3-9-19(10-4-14)25(21,22)20-12-18-11-15(20)13-24(18)17-7-5-16(23-2)6-8-17/h3-10,15,18H,11-13H2,1-2H3/t15-,18-,24?/m0/s1
InChI key   RMFZMNUGIFSNIE-YPAHSFBSSA-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 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 
Target organs 
Respiratory system
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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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

Related Products

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798339 Exo-1-Naphthyl Kwon [2.2.1] Bicyclic Phosphine
798363 Endo-Phenyl Kwon [2.2.1] Bicyclic Phosphine, 95% (HPLC)
798428 Endo-2-Naphthyl Kwon [2.2.1] Bicyclic Phosphine
798444 Endo-4-Methoxyphenyl Kwon [2.2.1] Bicyclic Phosphine
798436 Endo-1-Naphthyl Kwon [2.2.1] Bicyclic Phosphine
798371 Exo-Phenyl Kwon [2.2.1] Bicyclic Phosphine, 95% (HPLC)
798347 Exo-2-Naphthyl Kwon [2.2.1] Bicyclic Phosphine

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