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900811

Sigma-Aldrich

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

greener alternative

≥95%

Synonym(s):

(βS)-β-[[2,3-bis(dicyclohexylamino)-2-cyclopropen-1-ylidene]amino]-benzenepropanol hydrochloride (1:1), Dicyclohexyl cyclopropenimine, Lambert cyclopropenimine catalyst

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About This Item

Empirical Formula (Hill Notation):
C36H55N3O · HCl
CAS Number:
1366421-67-1
Molecular Weight:
582.30
MDL number:
MFCD22417240
UNSPSC Code:
12161600
NACRES:
NA.06

Quality Level

100

Assay

≥95%

form

powder or solid

reaction suitability

reagent type: catalyst
reaction type: Asymmetric synthesis

greener alternative product characteristics

Catalysis
Learn more about the Principles of Green Chemistry.

sustainability

Greener Alternative Product

functional group

amine
hydroxyl
imine
phenyl

greener alternative category

, Aligned

SMILES string

Cl.N(C6CCCCC6)(C5CCCCC5)C1=C(C1=NC(CO)Cc4ccccc4)N(C3CCCCC3)C2CCCCC2

InChI key

RTCSAEOYHXMTHG-UHFFFAOYSA-N

Related Categories

General description

We are committed to bringing you Greener Alternative Products, which adhere to one or more of The 12 Principles of Greener Chemistry. This product has been enhanced for catalytic efficiency. Click here for more information.

Application

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.

Other Notes

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

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Regulatory Listings

Regulatory Listings are mainly provided for chemical products. Only limited information can be provided here for non-chemical products. No entry means none of the components are listed. It is the user’s obligation to ensure the safe and legal use of the product.

JAN Code

900811-VAR:
900811-BULK:
900811-500MG:
900811-1G:

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Certificates of Analysis (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.
Jeffrey S Bandar et al.
Chemical science, 6(2), 1537-1547 (2015-10-28)
We recently demonstrated that chiral cyclopropenimines are viable Brønsted base catalysts in enantioselective Michael and Mannich reactions. Herein, we describe a series of structure-activity relationship studies that provide an enhanced understanding of the effectiveness of certain cyclopropenimines as enantioselective Brønsted
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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