Skip to Content
Merck
All Photos(1)

Key Documents

View All Documentation

798363

Sigma-Aldrich

Endo-Phenyl Kwon [2.2.1] Bicyclic Phosphine

95% (HPLC)

Synonym(s):

(1S,4S,5S)-5-(phenyl)-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):
C18H20NO2PS
Molecular Weight:
345.40
MDL number:
MFCD28016350
UNSPSC Code:
12352005
PubChem Substance ID:
329768643
NACRES:
NA.22

Quality Level

100

Assay

95% (HPLC)

form

powder

storage condition

under inert gas

mp

96-101 °C

storage temp.

2-8°C

SMILES string

O=S(N1C[C@@]2([H])[P@@](C3=CC=CC=C3)C[C@]1([H])C2)(C4=CC=C(C)C=C4)=O

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/t15-,17-,22?/m0/s1

InChI key

BWXYDSDVFPJTFY-TWMUNHRGSA-N

Looking for similar products? Visit Product Comparison Guide

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

H302

Precautionary Statements

P301 + P312 + P330

Hazard Classifications

Acute Tox. 4 Oral

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Choose from one of the most recent versions:

Certificates of Analysis (COA)

Lot/Batch Number
MKBT5973V

Don't see the Right Version?

If you require a particular version, you can look up a specific certificate by the Lot or Batch number.

Search for a COA

Already Own This Product?

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

Visit the Document Library

Lingchao Cai et al.
Journal of the American Chemical Society, 138(10), 3298-3301 (2016-02-26)
Described herein is a catalytic asymmetric total synthesis of (-)-actinophyllic acid, with the key step being a chiral phosphine-catalyzed [3 + 2] annulation between an imine and an allenoate to form a pyrroline intermediate in 99% yield and 94% ee.
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
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]
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

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