798371
Exo-Phenyl Kwon [2.2.1] Bicyclic Phosphine
95% (HPLC)
Synonym(s):
(1S,4S,5R)-5-(phenyl)-2-tosyl-2-aza-5-phosphabicyclo[2.2.1]heptane
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About This Item
Empirical Formula (Hill Notation):
C18H20NO2PS
Molecular Weight:
345.40
MDL number:
UNSPSC Code:
12352005
PubChem Substance ID:
NACRES:
NA.22
Quality Segment
assay
95% (HPLC)
form
powder
storage condition
under inert gas
mp
158-162 °C
functional group
phosphine, sulfonamide
storage temp.
2-8°C
SMILES string
CC1=CC=C(S(N2C[C@@]3([H])[P@](C4=CC=CC=C4)C[C@]2([H])C3)(=O)=O)C=C1
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
InChI key
BWXYDSDVFPJTFY-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
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signalword
Warning
hcodes
pcodes
Hazard Classifications
Acute Tox. 4 Oral
Storage Class
11 - Combustible Solids
wgk
WGK 3
flash_point_f
Not applicable
flash_point_c
Not applicable
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