Application

Metal-free OrganoCatalyst technology for asymmetric catalysis. Catalyzes asymmetric indole alkylations, Friedel-Crafts alkylations, and a broad range of conjugate addition reactions in high enantiomeric excess.

(2S,5S)-(-)-2-tert-Butyl-3-methyl-5-benzyl-4-imidazolidinone is a second-generation MacMillan catalyst, which can be used as a chiral organocatalyst in: The chiral transformation reaction, including Friedel-Crafts and Mukaiyama-Michael reactions. The preparation of substituted spiroundecenetriones via asymmetric domino Knoevenagel/Diels-Alder reactions. The asymmetric synthesis of β-hydroxy aldehydes and their dimethylacetals via aldehyde-aldehyde aldol condensation reaction. The enantioselective α-fluorination of aldehydes using N-fluorobenzenesulfonamide as a fluorinating agent. The stereoselective preparation of (oxomethyl)oxabicyclo[3.2.1]octenones and tricyclic pyrroles via [4+3] cycloaddition of (trialkylsiloxy)pentadienals to furans.

Features and Benefits

Advantages of MacMillan imidazolidinone organocatalysts:Superior enantiocontrol in numerous transformationsHigh activities at low catalyst loadingsExtraordinary functional group tolerance

General description

(2S,5S)-(-)-2-tert-Butyl-3-methyl-5-benzyl-4-imidazolidinone is a chiral imidazolidinone organocatalyst, developed by MacMillan and co-workers.

Legal Information

U.S. Pat. 6,369,243 and related patents apply. For research purposes only.

Packaging

1 g in glass bottle

500 mg in glass insert