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Sigma-Aldrich

Endo-1-Naphthyl Kwon [2.2.1] Bicyclic Phosphine

Synonym(e):

(1S,4S,5S)-5-(naphthalen-1-yl)-2-tosyl-2-aza-5-phosphabicyclo[2.2.1]heptane

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About This Item

Empirische Formel (Hill-System):
C22H22NO2PS
Molekulargewicht:
395.45
UNSPSC-Code:
12352000
PubChem Substanz-ID:
329768649
NACRES:
NA.22

Form

powder

Qualitätsniveau

100

Lagerbedingungen

under inert gas

Lagertemp.

2-8°C

SMILES String

O=S(N1C[C@H]2[P@@](C3=CC=CC4=C3C=CC=C4)C[C@@H]1C2)(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

InChIKey

RGHUOMJULXTHPX-UHFFFAOYSA-N

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Anwendung

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.

Sonstige Hinweise

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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Piktogramme

Exclamation mark
GHS07

Signalwort

Warning

Gefahreneinstufungen

Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3

Zielorgane

Respiratory system

Lagerklassenschlüssel

11 - Combustible Solids

WGK

WGK 3

Flammpunkt (°F)

Not applicable

Flammpunkt (°C)

Not applicable

Analysenzertifikate (COA)

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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

Artikel

Kwon Phosphines: P-Chiral Monodentate Phosphines from Hydroxyproline

Chiral phosphines have been the staple ligands for asymmetric transition metal catalysis and more recently operate as catalysts in organic phosphinocatalysis.

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