798347

Exo-2-Naphthyl Kwon [2.2.1] Bicyclic Phosphine

• Synonym(s): (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

Properties

• form: powder
• Quality Level: 100
• mp: 153-158 °C
• storage temp.: 2-8°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.

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