798746

Exo-4-anisole Kwon [2.2.1] bicyclic phosphine

• Synonym(s): Exo-4-Methoxyphenyl Kwon [2.2.1] Bicyclic Phosphine, (1S,4S,5R)-5-(4-methoxyphenyl)-2-tosyl-2-aza-5-phosphabicyclo[2.2.1]heptane
• Empirical Formula (Hill Notation): C₁₉H₂₂NO₃PS
• Molecular Weight: 375.42
• MDL number: MFCD28016352
• UNSPSC Code: 12352005
• PubChem Substance ID: 329768668
• NACRES: NA.22

Properties

• form: powder
• Quality Level: 100
• mp: 85-90 °C
• SMILES string: O=S(N1C[C@@]2([H])[P@](C3=CC=C(OC)C=C3)C[C@]1([H])C2)(C4=CC=C(C)C=C4)=O
• InChI: 1S/C19H22NO3PS/c1-14-3-9-19(10-4-14)25(21,22)20-12-18-11-15(20)13-24(18)17-7-5-16(23-2)6-8-17/h3-10,15,18H,11-13H2,1-2H3/t15-,18-,24?/m0/s1
• InChI key: RMFZMNUGIFSNIE-YPAHSFBSSA-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