SLAP reagents for the photocatalytic synthesis of C3/C5-substituted, N-unprotected selenomorpholines and 1,4-selenazepanes

Abstract

Herein, we disclose the first set of unique selenium-containing SLAP (SiLicon Amine Protocol) reagents for the direct synthesis of C3/C5-substituted selenomorpholines and 1,4-selenazepanes from diverse (hetero)aldehydes under mild photocatalytic conditions. Enantiomerically pure 1,2-amino alcohol/α-amino acid versions of these heterocycles were also synthesized. Further, we have shown the late-stage modification of certain biologically active agents using the developed seleno-SLAP reagents.