798339

Sigma-Aldrich

Exo-1-Naphthyl Kwon [2.2.1] Bicyclic Phosphine

Sinónimos:
(1S,4S,5R)-5-(naphthalen-1-yl)-2-tosyl-2-aza-5-phosphabicyclo[2.2.1]heptane
Empirical Formula (Hill Notation):
C22H22NO2PS
Peso molecular:
395.45
Número MDL:
ID de la sustancia en PubChem:
NACRES:
NA.22

formulario

powder

Nivel de calidad

100

condiciones de almacenamiento

under inert gas

temp. de almacenamiento

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

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Aplicación

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.

Envase

100 mg in glass bottle

pictogramas

Exclamation mark

Palabra de señalización

Warning

Frases de peligro

Órganos de actuación

Respiratory system

RIDADR

NONH for all modes of transport

WGK Alemania

WGK 3

Punto de inflamabilidad F

Not applicable

Punto de inflamabilidad C

Not applicable

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...
Artículos
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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Contenido relacionado
The Kwon Group has made major strides in the development and application of nucleophilic phosphinocatalysis reactions as a means to synthesize carbo- and heterocycles that serve as synthetic intermediates for both natural products and medicinally useful compounds.
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