798363

Endo-Phenyl Kwon [2.2.1] Bicyclic Phosphine

95% (HPLC)

• Synonym(s): (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

Properties

• 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.

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
• Signal Word: Warning
• Hazard Statements: H302
• Precautionary Statements: P301 + P312 + P330
• Hazard Classifications: Acute Tox. 4 Oral
• Storage Class Code: 13 - Non Combustible Solids
• WGK: WGK 3
• Flash Point(F): Not applicable
• Flash Point(C): Not applicable