Alkylation of isatins with trichloroacetimidates.

-Alkylation of isatins can be achieved utilizing trichloroacetimidate electrophiles and a Lewis acid catalyst. These reactions provide access to -alkyl isatins, versatile scaffolds which are often employed in the synthesis of pharmaceutical lead structures as well as natural products. Secondary trichloroacetimidates that are precursors to stabilized carbocations provided excellent yields of the isatin product.

Formation of Pyrroloindolines the Alkylation of Tryptamines with Trichloroacetimidates.

Pyrroloindolines and related systems are present in a large number of complex natural products. These core structures have generated considerable synthetic interest, as many of the compounds possess challenging, elaborate structures and interesting biological properties. Recently we have focused on using trichloroacetimidates for the synthesis of these fascinating molecules.