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Merck
CN
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文件

900811

Sigma-Aldrich

(S)-2-(2,3-Bis(dicyclohexylamino)cyclopropenimine)-3-phenylpropan-1-ol hydrochloride

greener alternative

≥95%

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所有图片(4)
别名:
(βS)-β-[[2,3-bis(dicyclohexylamino)-2-cyclopropen-1-ylidene]amino]-benzenepropanol hydrochloride (1:1), Dicyclohexyl cyclopropenimine, Lambert cyclopropenimine catalyst
经验公式（希尔记法）:
C36H55N3O · HCl
CAS号:
1366421-67-1
分子量:
582.30
UNSPSC代码:
12352200
NACRES:
NA.06

质量水平

100

检测方案

≥95%

形式

powder or solid

反应适用性

reagent type: catalyst
reaction type: Asymmetric synthesis

环保替代产品特性

Catalysis
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sustainability

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环保替代产品分类

, Aligned

相关类别

一般描述

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应用

Chiral cyclopropenimines are a highly effective new class of enantioselective Brønsted base catalysts - the so-called “superbases” for enantioselective organocatalysis. Due to the prevalence of chemical reactions involving proton transfer as a key mechanistic event, Brønsted bases have become indispensable tools for the practice of organic synthetic chemistry, capable of catalyzing proton transfer reactions enantioselectively for the production of optically enriched products. Catalyst is stored as co-salt for stability. Conversion of the HCl salt to free catalyst requires a simple wash with aqueous base. This is one of a suite of Brønsted catalysts reported by Tristan Lambert and coworkers available through Sigma-Aldrich.

其他说明

Enantioselective Bronsted Base Catalysis with Chiral Cyclopropenimines

Cyclopropenimine-Catalyzed Enantioselective Mannich Reactions of tert-Butyl Glycinates with N-Boc-Imines

Transition State Analysis of Enantioselective Bronsted Base Catalysis by Chiral Cyclopropenimines

Structure-activity relationship studies of cyclopropenimines as enantioselective Bronsted base catalysts

Asymmetric Bronsted Base-Catalyzed and -Directed [3+2] Cycloaddition of 2-Acyl Cycloheptatrienes with Azomethine Ylides

WGK

WGK 3

闪点(°F)

Not applicable

闪点(°C)

Not applicable

分析证书(COA)

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Jeffrey S Bandar et al.
Journal of the American Chemical Society, 136(30), 10700-10707 (2014-07-17)
Experimental (13)C kinetic isotope effects have been used to interrogate the rate-limiting step of the Michael addition of glycinate imines to benzyl acrylate catalyzed by a chiral 2,3-bis(dicyclohexylamino) cyclopropenimine catalyst. The reaction is found to proceed via rate-limiting carbon-carbon bond
Jeffrey S Bandar et al.
Journal of the American Chemical Society, 135(32), 11799-11802 (2013-08-03)
Cyclopropenimine 1 is shown to catalyze Mannich reactions between glycine imines and N-Boc-aldimines with high levels of enantio- and diastereocontrol. The reactivity of 1 is shown to be substantially greater than that of a widely used thiourea cinchona alkaloid-derived catalyst.
Vibeke H Lauridsen et al.
Chemistry (Weinheim an der Bergstrasse, Germany), 22(10), 3259-3263 (2016-01-26)
Conjugated cyclic trienes have the potential for different types of cycloaddition reactions. In the present work, we will, in a novel asymmetric cycloaddition reaction, demonstrate that the organocatalytic reaction of 2-acyl cycloheptatrienes with azomethine ylides proceeds as a [3+2] cycloaddition
Jeffrey S Bandar et al.
Journal of the American Chemical Society, 134(12), 5552-5555 (2012-03-16)
Cyclopropenimines are shown to be a highly effective new class of enantioselective Brønsted base catalysts. A chiral 2,3-bis(dialkylamino)cyclopropenimine catalyzes the rapid Michael reaction of a glycine imine substrate with high levels of enantioselectivity. A preparative scale reaction to deliver 25

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