798339

Exo-1-Naphthyl Kwon [2.2.1] Bicyclic Phosphine

• Synonym(s): (1S,4S,5R)-5-(naphthalen-1-yl)-2-tosyl-2-aza-5-phosphabicyclo[2.2.1]heptane
• Empirical Formula (Hill Notation): C₂₂H₂₂NO₂PS
• Molecular Weight: 395.45
• MDL number: MFCD28016349
• UNSPSC Code: 12352005
• PubChem Substance ID: 329768640
• NACRES: NA.22

Properties

• form: powder
• Quality Level: 100
• storage condition: under inert gas
• functional group: phosphine; sulfonamide
• storage temp.: 2-8°C
• SMILES string: O=S(N1C[C@@]2([H])[P@](C3=CC=CC4=C3C=CC=C4)C[C@]1([H])C2)(C5=CC=C(C)C=C5)=O
• InChI: 1S/C22H22NO2PS/c1-16-9-11-20(12-10-16)27(24,25)23-14-19-13-18(23)15-26(19)22-8-4-6-17-5-2-3-7-21(17)22/h2-12,18-19H,13-15H2,1H3/t18-,19-,26?/m0/s1
• InChI key: RGHUOMJULXTHPX-OCOBAGFRSA-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: H315,H319,H335
• Precautionary Statements: P261 - P264 - P271 - P280 - P302 + P352 - P305 + P351 + P338
• Hazard Classifications: Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3
• Target Organs: Respiratory system
• Storage Class Code: 11 - Combustible Solids
• WGK: WGK 3
• Flash Point(F): Not applicable
• Flash Point(C): Not applicable