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文件

798428

Endo-2-Naphthyl Kwon [2.2.1] Bicyclic Phosphine

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

别名:

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

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About This Item

经验公式（希尔记法）:

C₂₂H₂₂NO₂PS

分子量:

395.45

分類程式碼代碼:

12352000

PubChem物質ID:

329768648

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Sigma-Aldrich

798436

Endo-1-Naphthyl Kwon [2.2.1] Bicyclic Phosphine

Sigma-Aldrich

745685

2-(Bromomethyl)oxetane

Sigma-Aldrich

715263

N-Boc-1H-吡唑-4-硼酸

Sigma-Aldrich

700762

(S)-SIPHOS-PE

Sigma-Aldrich

237655

(-)-2,3-O-异丙烯基-2,3-二羟基-1,4-双(二苯基膦)丁烷

Sigma-Aldrich

668192

(S)-(+)-(3,5-二氧-4-磷-环庚并[2,1-a;3,4- a′]二萘-4-基)二甲胺

Sigma-Aldrich

88717

(R)-(-)-1-[(S)-2-二苯基磷]二茂铁乙基二环己基磷

Sigma-Aldrich

QBD11155

DOTA-tris(TBE)-amido-dPEG ^®₄-TFP ester

Sigma-Aldrich

798347

Exo-2-Naphthyl Kwon [2.2.1] Bicyclic Phosphine

Sigma-Aldrich

681571

(6-溴己基)二茂铁

形狀

powder

儲存溫度

2-8°C

SMILES 字串

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

InChI 密鑰

SJQXCVUHXMHJMD-UHFFFAOYSA-N

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應用

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.

訊號詞

Warning

危險聲明

H315,H319,H335

防範說明

P261 - P264 - P271 - P280 - P302 + P352 - P305 + P351 + P338

危險分類

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

標靶器官

Respiratory system

儲存類別代碼

11 - Combustible Solids

水污染物質分類（WGK）

WGK 3

閃點（°F）

Not applicable

閃點（°C）

Not applicable

分析证书(COA)

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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

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]

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

商品

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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