10.1002/chem.201002563
The research primarily focuses on the development of an asymmetric conjugate addition reaction of 3-substituted oxindoles to 2-chloroacrylonitrile, utilizing a chiral alkyl thiourea as a catalyst. This reaction is significant for the construction of chiral pyrroloindoline structures, which are key components in many biologically active indole alkaloids. The experiments involved screening various bifunctional tertiary amine thioureas or urea catalysts to optimize the reaction conditions, ultimately achieving high yields and excellent stereoselectivity. Reactants included 3-substituted oxindoles and 2-chloroacrylonitrile, with the catalysts being screened at low temperatures. Analyses used to determine the success of the reactions included 1H NMR spectroscopy for diastereomeric ratios and chiral HPLC analysis for enantiomeric excess. The optimized conditions were identified as using 4a catalyst in 1,2-dichloroethane at -20°C with 4 ? molecular sieves, yielding products with up to >30:1 dr and up to 99% ee.