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Merck
CN
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文件

798363

Sigma-Aldrich

Endo-Phenyl Kwon [2.2.1] Bicyclic Phosphine

95% (HPLC)

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别名:
(1S,4S,5S)-5-(phenyl)-2-tosyl-2-aza-5-phosphabicyclo[2.2.1]heptane
经验公式（希尔记法）:
C18H20NO2PS
分子量:
345.40
MDL编号:
MFCD28016350
UNSPSC代码:
12352005
PubChem化学物质编号:
329768643
NACRES:
NA.22

质量水平

100

检测方案

95% (HPLC)

形式

powder

储存条件

under inert gas

mp

96-101 °C

储存温度

2-8°C

SMILES字符串

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

InChI

1S/C18H20NO2PS/c1-14-7-9-18(10-8-14)23(20,21)19-12-17-11-15(19)13-22(17)16-5-3-2-4-6-16/h2-10,15,17H,11-13H2,1H3/t15-,17-,22?/m0/s1

InChI key

BWXYDSDVFPJTFY-TWMUNHRGSA-N

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应用

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.

其他说明

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

象形图

Exclamation mark
GHS07

警示用语：

Warning

危险声明

H302

预防措施声明

P301 + P312 + P330

危险分类

Acute Tox. 4 Oral

WGK

WGK 3

闪点(°F)

Not applicable

闪点(°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.
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]
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
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

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.

相关内容

Kwon Group – Professor Product Portal

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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