798355
Exo-4-Fluorophenyl Kwon [2.2.1] Bicyclic Phosphine
Synonym(s):
(1S,4S,5R)-5-(4-fluorophenyl)-2-tosyl-2-aza-5-phosphabicyclo[2.2.1]heptane
Sign In to View Organizational & Contract Pricing.
Select a Size
Change View
About This Item
Empirical Formula (Hill Notation):
C18H19FNO2PS
Molecular Weight:
363.39
PubChem Substance ID:
UNSPSC Code:
12352101
form
powder
storage temp.
2-8°C
SMILES string
FC(C=C1)=CC=C1[P@]2[C@]3([H])CN(S(C4=CC=C(C)C=C4)(=O)=O)[C@](C3)([H])C2
InChI
1S/C18H19FNO2PS/c1-13-2-8-18(9-3-13)24(21,22)20-11-17-10-15(20)12-23(17)16-6-4-14(19)5-7-16/h2-9,15,17H,10-12H2,1H3
InChI key
UPOWUYAESRCGIJ-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
Choose from one of the most recent versions:
Already Own This Product?
Find documentation for the products that you have recently purchased in the Document Library.
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
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