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4-Dimethylaminopyridine (DMAP) is a derivative of pyridine with the chemical formula (CH 3) 2 NC 5 H 4 N. This white solid is of interest because it is more basic than pyridine , owing to the resonance stabilisation from the NMe 2 substituent.
DMAP may refer to: Digital Media Access Protocol, a family of proprietary protocols by Apple; 4-Dimethylaminopyridine (CH 3) 2 NC 5 H 4 N), a derivative of pyridine; 4-Dimethylaminophenol (C 8 H 11 NO), an aromatic compound containing both phenol and amine functional groups; Data Management Advisory Panel, of the England school census
The reactivity of anhydrides can be increased by using a catalytic amount of N,N-dimethylaminopyridine ("DMAP") or even pyridine. [12] First, DMAP (2) attacks the anhydride (1) to form a tetrahedral intermediate, which collapses to eliminate a carboxylate ion to give amide 3. This intermediate amide is more activated towards nucleophilic attack ...
Add the amine to di-tert-butyl dicarbonate, 4-dimethylaminopyridine (DMAP), and acetonitrile (MeCN) at ambient temperature [15] BOC-protected amines are prepared using the reagent di-tert-butyl-iminodicarboxylate. Upon deprotonation, this reagent affords a doubly BOC-protected source of NH − 2, which can be N-alkylated.
The Yamaguchi esterification is the chemical reaction of an aliphatic carboxylic acid and 2,4,6-trichlorobenzoyl chloride (TCBC, Yamaguchi reagent) to form a mixed anhydride which, upon reaction with an alcohol in the presence of stoichiometric amount of DMAP, produces the desired ester. It was first reported by Masaru Yamaguchi et al. in 1979 ...
First, the carbonyl of the acid attacks the carbodiimide of EDC, and there is a subsequent proton transfer. The primary amine then attacks the carbonyl carbon of the acid which forms a tetrahedral intermediate before collapsing and discharging the urea byproduct. The desired amide is obtained. [6]
As a reagent in organic chemistry, DBU is used as a ligand and base. As a base, protonation occurs at the imine nitrogen. [5] Lewis acids also attach to the same nitrogen. [6] These properties recommend DBU for use as a catalyst, for example as a curing agent for epoxy resins and polyurethane.
For example, for two complementary reactions both with s=49, 100% conversion would give products in 50% yield and 96% ee. These same values would require s=200 for a simple kinetic resolution. As such, the promise of PKR continues to attract much attention. The Kishi CBS reduction remains one of the few examples to fulfill this promise.