Module 10 : Organocatalysis

Lecture 35: Alkaloid Based Reactions

10.2.4 Hydroxyalkylation Reaction

The readily available cinchonidine (CD) and cinchonine (CN) can be used for the catalysis of the hydroxyalkylation of heteroaromatics. For example, the hydroxyalkylation of indoles with ethyl-3,3,3-trifluropyruvate occurs to afford corresponding 3-substituted products in high yields and ee values (Scheme 14) .

Scheme 14. Hydroxyalkylation of Indoles with Ethyl-3,3,3-trifluropyruvate