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798347 Sigma-Aldrich

Exo-2-Naphthyl Kwon [2.2.1] Bicyclic Phosphine

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

  • Empirical Formula (Hill Notation) C22H22NO2PS

  • Molecular Weight 395.45

  •  PubChem Substance ID 329768641

  •  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
form   powder
mp   153-158 °C
SMILES string   O=S(N1C[C@H]2[P@](C3=CC=C4C(C=CC=C4)=C3)C[C@@H]1C2)(C5=CC=C(C)C=C5)=O
InChI   1S/C22H22NO2PS/c1-16-6-10-22(11-7-16)27(24,25)23-14-21-13-19(23)15-26(21)20-9-8-17-4-2-3-5-18(17)12-20/h2-12,19,21H,13-15H2,1H3
InChI key   SJQXCVUHXMHJMD-UHFFFAOYSA-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 
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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798436 Endo-1-Naphthyl Kwon [2.2.1] Bicyclic Phosphine
798371 Exo-Phenyl Kwon [2.2.1] Bicyclic Phosphine, 95% (HPLC)
798746 Exo-4-anisole Kwon [2.2.1] bicyclic phosphine

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