Skip to Content
Merck
All Photos(1)

Key Documents

View All Documentation

798339

Sigma-Aldrich

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

Sign Into View Organizational & Contract Pricing
All Photos(1)

About This Item

Empirical Formula (Hill Notation):
C22H22NO2PS
Molecular Weight:
395.45
MDL number:
MFCD28016349
UNSPSC Code:
12352005
PubChem Substance ID:
329768640
NACRES:
NA.22

form

powder

Quality Level

100

storage condition

under inert gas

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

Looking for similar products? Visit Product Comparison Guide

Related Categories

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

Pictograms

Exclamation mark
GHS07

Signal Word

Warning

Hazard Statements

H315,H319,H335

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

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

Already Own This Product?

Find documentation for the products that you have recently purchased in the Document Library.

Visit the Document Library

Yiting Gu et al.
Journal of the American Chemical Society, 137(19), 6400-6406 (2015-04-24)
Two classes of phosphine-catalyzed addition/cycloaddition domino reactions of β'-acetoxy allenoate 1 have been developed. The reaction of 1 with 2-acyl-3-methyl-acrylonitrile 2 readily occurs to give 2-oxabicyclo[3.3.1]nonane 3, furnishing the β'-addition/[4 + 4] cycloaddition domino sequence. In this sequence, β'C of
Christopher E Henry et al.
Journal of the American Chemical Society, 136(34), 11890-11893 (2014-08-08)
We have prepared two new diastereoisomeric 2-aza-5-phosphabicyclo[2.2.1]heptanes from naturally occurring trans-4-hydroxy-L-proline in six chemical operations. These syntheses are concise and highly efficient, with straightforward purification. When we used these chiral phosphines as catalysts for reactions of γ-substituted allenoates with imines
Ian P Andrews et al.
Chemical science, 3(8), 2510-2514 (2012-07-17)
In this study we performed the total synthesis of the terpene indole alkaloid (+)-ibophyllidine through a pathway involving asymmetric phosphine catalysis, with our novel l-4-hydroxyproline-derived chiral phosphine mediating the key [3 + 2] annulation. Hydrogenation of the [3 + 2]

Our team of scientists has experience in all areas of research including Life Science, Material Science, Chemical Synthesis, Chromatography, Analytical and many others.

Contact Technical Service