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Key Documents

Ursprungszeugnis (CoO)/Analysenzertifikate (CoA)

Weitere Dokumente

798347

Exo-2-Naphthyl Kwon [2.2.1] Bicyclic Phosphine

Name: Exo-2-Naphthyl Kwon [2.2.1] Bicyclic Phosphine
Brand: ALDRICH

Synonym(e):

(1S,4S,5R)-5-(naphthalen-2-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:

329768641

NACRES:

NA.22

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Sigma-Aldrich

798371

Exo-Phenyl Kwon [2.2.1] Bicyclic Phosphine

Sigma-Aldrich

798363

Endo-Phenyl Kwon [2.2.1] Bicyclic Phosphine

Sigma-Aldrich

694215

(S,S)-2,3-Bis(tert-butylmethylphosphino)chinoxalin

Sigma-Aldrich

676403

(R,R)-(-)-2,3-Bis(tert-Butylmethylphosphino)chinoxalin

Sigma-Aldrich

798436

Endo-1-Naphthyl Kwon [2.2.1] Bicyclic Phosphine

Sigma-Aldrich

798444

Endo-4-Methoxyphenyl Kwon [2.2.1] Bicyclic Phosphine

Sigma-Aldrich

798746

Exo-4-anisole Kwon [2.2.1] bicyclic phosphine

Sigma-Aldrich

682144

(R)-(-)-4,12-Bis(diphenylphosphino)-[2.2]-Paracyclophan

Sigma-Aldrich

667811

(−)-1,2-Bis((2R,5R)-2,5-Diphenylphospholano)ethan

Sigma-Aldrich

667854

(+)-1,2-Bis((2S,5S)-2,5-Diphenylphospholano)ethan

Form

powder

Qualitätsniveau

100

mp (Schmelzpunkt)

153-158 °C

Lagertemp.

2-8°C

SMILES String

O=S(N1C[C@H]2[P@](C3=CC=C4C(C=CC=C4)=C3)C[C@@H]1C2)(C5=CC=C(C)C=C5)=O

InChI

1S/C22H22NO2PS/c1-16-6-10-22(11-7-16)27(24,25)23-14-21-13-19(23)15-26(21)20-9-8-17-4-2-3-5-18(17)12-20/h2-12,19,21H,13-15H2,1H3

InChIKey

SJQXCVUHXMHJMD-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.

Signalwort

Warning

H-Sätze

H302

P-Sätze

P301 + P312 + P330

Gefahreneinstufungen

Acute Tox. 4 Oral

Lagerklassenschlüssel

11 - Combustible Solids

WGK

WGK 3

Flammpunkt (°F)

Not applicable

Flammpunkt (°C)

Not applicable

Analysenzertifikate (COA)

Suchen Sie nach Analysenzertifikate (COA), indem Sie die Lot-/Chargennummer des Produkts eingeben. Lot- und Chargennummern sind auf dem Produktetikett hinter den Wörtern ‘Lot’ oder ‘Batch’ (Lot oder Charge) zu finden.

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Phosphine-Catalyzed Addition/Cycloaddition Domino Reactions of β'-Acetoxy Allenoate: Highly Stereoselective Access to 2-Oxabicyclo[3.3.1]nonane and Cyclopenta[a]pyrrolizine.

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

Enantioselective total synthesis of (+)-ibophyllidine via an asymmetric phosphine-catalyzed [3 + 2] annulation.

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]

Hydroxyproline-derived pseudoenantiomeric [2.2.1] bicyclic phosphines: asymmetric synthesis of (+)- and (-)-pyrrolines.

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.

Key Documents

Exo-2-Naphthyl Kwon [2.2.1] Bicyclic Phosphine

About This Item

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Eigenschaften

Form

Qualitätsniveau

mp (Schmelzpunkt)

Lagertemp.

SMILES String

InChI

InChIKey

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Beschreibung

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798363

798428

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798371

798746

Sicherheitshinweise

Piktogramme

Signalwort

H-Sätze

P-Sätze

Gefahreneinstufungen

Lagerklassenschlüssel

WGK

Flammpunkt (°F)

Flammpunkt (°C)

Dokumentation

Analysenzertifikate (COA)

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