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798444

Sigma-Aldrich

Endo-4-Methoxyphenyl Kwon [2.2.1] Bicyclic Phosphine

Sinonimo/i:

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

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About This Item

Formula empirica (notazione di Hill):
C19H22NO3PS
Peso molecolare:
375.42
Codice UNSPSC:
12352005
ID PubChem:
329768650
NACRES:
NA.22

Forma fisica

powder

Livello qualitativo

100

Punto di fusione

156-161 °C

Gruppo funzionale

phosphine
sulfonamide

Temperatura di conservazione

2-8°C

Stringa SMILE

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

InChI

1S/C19H22NO3PS/c1-14-3-9-19(10-4-14)25(21,22)20-12-18-11-15(20)13-24(18)17-7-5-16(23-2)6-8-17/h3-10,15,18H,11-13H2,1-2H3
RMFZMNUGIFSNIE-UHFFFAOYSA-N

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Applicazioni

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.

Altre note

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

Prodotti correlati

N° Catalogo
Descrizione
Determinazione del prezzo

Pittogrammi

Exclamation mark
GHS07

Avvertenze

Warning

Indicazioni di pericolo

H315,H319,H335

Classi di pericolo

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

Organi bersaglio

Respiratory system

Codice della classe di stoccaggio

11 - Combustible Solids

Classe di pericolosità dell'acqua (WGK)

WGK 3

Punto d’infiammabilità (°F)

Not applicable

Punto d’infiammabilità (°C)

Not applicable

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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

Articoli

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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