798444
Endo-4-Methoxyphenyl Kwon [2.2.1] Bicyclic Phosphine
Synonym(s):
(1S,4S,5S)-5-(4-methoxyphenyl)-2-tosyl-2-aza-5-phosphabicyclo[2.2.1]heptane
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About This Item
Empirical Formula (Hill Notation):
C19H22NO3PS
Molecular Weight:
375.42
MDL number:
UNSPSC Code:
12352005
PubChem Substance ID:
NACRES:
NA.22
form
powder
Quality Segment
mp
156-161 °C
functional group
phosphine, sulfonamide
storage temp.
2-8°C
SMILES string
O=S(N1C[C@H]2[P@@](C3=CC=C(OC)C=C3)C[C@@H]1C2)(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
InChI key
RMFZMNUGIFSNIE-UHFFFAOYSA-N
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
Technology Spotlight- Kwon Phosphines: P-Chiral Monodentate Phosphines from Hydroxyproline
Aldrichimica Acta Review- Nucleophilic Chiral Phosphines: Powerful and Versatile Catalysts for Asymmetric Annulations
signalword
Warning
hcodes
Hazard Classifications
Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3
target_organs
Respiratory system
Storage Class
11 - Combustible Solids
wgk
WGK 3
flash_point_f
Not applicable
flash_point_c
Not applicable
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