900811
(S)-2-(2,3-Bis(dicyclohexylamino)cyclopropenimine)-3-phenylpropan-1-ol hydrochloride
≥95%
Synonym(s):
(βS)-β-[[2,3-bis(dicyclohexylamino)-2-cyclopropen-1-ylidene]amino]-benzenepropanol hydrochloride (1:1), Dicyclohexyl cyclopropenimine, Lambert cyclopropenimine catalyst
Sign Into View Organizational & Contract Pricing
All Photos(4)
About This Item
Empirical Formula (Hill Notation):
C36H55N3O · HCl
CAS Number:
Molecular Weight:
582.30
UNSPSC Code:
12161600
NACRES:
NA.06
Recommended Products
Quality Level
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
greener alternative category
, Aligned
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
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
Certificates of Analysis (COA)
Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.
Already Own This Product?
Find documentation for the products that you have recently purchased in the Document Library.
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, 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.
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, 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
Our team of scientists has experience in all areas of research including Life Science, Material Science, Chemical Synthesis, Chromatography, Analytical and many others.
Contact Technical Service