Dialkylation of Indoles with Trichloroacetimidates to Access 3,3-Disubstituted Indolenines

Abstract

2-Substituted indoles may be directly transformed to 3,3-dialkyl indolenines with trichloroacetimidate electrophiles and the Lewis acid TMSOTf. These reactions provide rapid access to complex indolenines which are present in a variety of complex natural products and medicinally relevant small molecule structures. This method provides an alternative to the use of transition metal catalysis. The indolenines are readily transformed into spiroindoline systems which are privileged scaffolds in medicinal chemistry.

Keywords

• indole
• dialkylation
• indolenine
• trichloroacetimidate
• spiroindoline