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  • 900811 - (S)-2-(2,3-Bis(dicyclohexylamino)cyclopropenimine)-3-phenylpropan-1-ol hydrochloride

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900811 Sigma-Aldrich

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

Green Alternative

≥95%

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

  • CAS Number 1366421-67-1

  • Empirical Formula (Hill Notation) C36H55N3O · HCl

  • Molecular Weight 582.30

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Properties

Related Categories 12 Principles Aligned Products, Asymmetric Synthesis, Catalysis and Inorganic Chemistry, Chemical Synthesis, Chiral Catalysts, Ligands, and Reagents,
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.
greener alternative category   Aligned

Description

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

Safety & Documentation

Safety Information

RIDADR 
NONH for all modes of transport
WGK Germany 
WGK 3
Flash Point(F) 
Not applicable
Flash Point(C) 
Not applicable

Documents

Certificate of Analysis (COA)

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Protocols & Articles
Peer-Reviewed Papers
15

References

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