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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

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Size/SKUAvailabilityPrice
100 mg

Available to ship TODAYfromMILWAUKEE

$126.00
$94.50

About This Item

Empirical Formula (Hill Notation):
C22H22NO2PS
Molecular Weight:
395.45
MDL number:
MFCD28016353
UNSPSC Code:
12352000
PubChem Substance ID:
329768641
NACRES:
NA.22

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form

powder

Quality Segment

100

mp

153-158 °C

functional group

phosphine, sulfonamide

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

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

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This Item
798339798436798371
Exo-2-Naphthyl Kwon [2.2.1] Bicyclic Phosphine

Sigma-Aldrich

798347

Exo-2-Naphthyl Kwon [2.2.1] Bicyclic Phosphine

Exo-1-Naphthyl Kwon [2.2.1] Bicyclic Phosphine

Sigma-Aldrich

798339

Exo-1-Naphthyl Kwon [2.2.1] Bicyclic Phosphine

Endo-1-Naphthyl Kwon [2.2.1] Bicyclic Phosphine

Sigma-Aldrich

798436

Endo-1-Naphthyl Kwon [2.2.1] Bicyclic Phosphine

Exo-Phenyl Kwon [2.2.1] Bicyclic Phosphine 95% (HPLC)

Sigma-Aldrich

798371

Exo-Phenyl Kwon [2.2.1] Bicyclic Phosphine

form

powder

form

powder

form

powder

form

powder

functional group

phosphine, sulfonamide

functional group

phosphine, sulfonamide

functional group

phosphine, sulfonamide

functional group

phosphine, sulfonamide

Quality Level

100

Quality Level

100

Quality Level

100

Quality Level

100

storage temp.

2-8°C

storage temp.

2-8°C

storage temp.

2-8°C

storage temp.

2-8°C

mp

153-158 °C

mp

-

mp

-

mp

158-162 °C

pictograms

Exclamation mark
GHS07

signalword

Warning

hcodes

H302

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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