Atroposelective Nenitzescu Indole Synthesis

Abstract

AbstractIn the past decade, compounds bearing a stereogenic C−N axis have gained significant attention in fields ranging from ligand to drug design. Yet, the atroposelective synthesis of these molecules remains a considerable challenge. In contrast to recent methods using more advanced chiral catalysts, a very simply accessed Jacobsen‐type chromium(III)−salen complex was used here as a chiral enantiopure Lewis acid catalyst for a highly atroposelective Nenitzescu indole synthesis. Mild reaction conditions afforded various 5‐hydroxybenzo[g]indoles in up to 97 % yield. Moreover, through a simple work‐up, very high enantiomeric excesses of up to 99 % could be obtained.