798371

Exo-Phenyl Kwon [2.2.1] Bicyclic Phosphine

95% (HPLC)

• Synonym(s): (1S,4S,5R)-5-(phenyl)-2-tosyl-2-aza-5-phosphabicyclo[2.2.1]heptane
• Empirical Formula (Hill Notation): C₁₈H₂₀NO₂PS
• Molecular Weight: 345.40
• MDL number: MFCD28016350
• UNSPSC Code: 12352005
• PubChem Substance ID: 329768644
• NACRES: NA.22

Properties

• Quality Level: 100
• assay: 95% (HPLC)
• form: powder
• storage condition: under inert gas
• mp: 158-162 °C
• functional group: phosphine; sulfonamide
• storage temp.: 2-8°C
• SMILES string: CC1=CC=C(S(N2C[C@@]3([H])[P@](C4=CC=CC=C4)C[C@]2([H])C3)(=O)=O)C=C1
• 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
• InChI key: BWXYDSDVFPJTFY-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.

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 Information

• pictograms: GHS07
• signalword: Warning
• hcodes: H302
• pcodes: P301 + P312 + P330
• Hazard Classifications: Acute Tox. 4 Oral
• Storage Class: 11 - Combustible Solids
• wgk_germany: WGK 3
• flash_point_f: Not applicable
• flash_point_c: Not applicable