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798355

Sigma-Aldrich

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

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About This Item

Empirical Formula (Hill Notation):
C18H19FNO2PS
Molecular Weight:
363.39
UNSPSC Code:
12352101
PubChem Substance ID:
329768642

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

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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

signalword

Warning

hcodes

H302

Hazard Classifications

Acute Tox. 4 Oral

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

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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

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