Organocatalyzed Asymmetric Alkylation of Stable Aryl or Heteroaryl(3-indolyl)methylium o-Benzenedisulfonimides

Stable diarylcarbenium salts, obtained by the direct coupling of indole or indole derivatives with aryl (or heteroaryl) aldehydes in the presence of a strong organic Brønsted acid, have been employed in the direct alkylation of aldehydes. Excellent enantiomeric excesses and good dr ratios were obtained using a number of aryl or heteroaryl(3-indolyl)carbenium ions as the highly stable o-benzenedisulfonimide salts and with the reaction promoted by the Hayashi-Jørgensen catalyst. A one-pot three-component stereoselective alkylation of aldehydes affording the same compounds was also investigated with various aldehydes, indole derivatives and organocatalysts. The results obtained with the isolated carbenium ions were superior in terms of yields and stereoselectivity.