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Synonyms: (betaS)-beta-[[2,3-bis(dicyclohexylamino)-2-cyclopropen-1-ylidene]amino]-benzenepropanol hydrochloride (1:1); Dicyclohexyl cyclopropenimine; Lambert cyclopropenimine catalyst
Molecular Formula: C36H55N3O · HCl
Molecular Weight: 582.3
Linear Structural Formula: C36H55N3O · HCl
Purity: >=95%
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 CyclopropeniminesCyclopropenimine-Catalyzed Enantioselective Mannich Reactions of tert-Butyl Glycinates with N-Boc-IminesTransition State Analysis of Enantioselective Bronsted Base Catalysis by Chiral CyclopropeniminesStructure-activity relationship studies of cyclopropenimines as enantioselective Bronsted base catalystsAsymmetric Bronsted Base-Catalyzed and -Directed [3+2] Cycloaddition of 2-Acyl Cycloheptatrienes with Azomethine Ylides