Atroposelective Nenitzescu Indole Synthesis

Chemistry - A European Journal, vol. 29, pp. e202300279

Abstract

In 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.

Authors 3

1. Vinzenz Thönnißen Aachen Institute of Organic Chemistry

   RWTH Aachen University

   Affiliation as printed

   Institute of Organic Chemistry RWTH Aachen University Landoltweg 1 52074 Aachen Germany

   Institute of Organic Chemistry, RWTH Aachen University, Landoltweg 1, 52074 Aachen, Germany

2. Iuliana L. Atodiresei Aachen Institute of Organic Chemistry

   RWTH Aachen University

   Affiliation as printed

   Institute of Organic Chemistry RWTH Aachen University Landoltweg 1 52074 Aachen Germany

   Institute of Organic Chemistry, RWTH Aachen University, Landoltweg 1, 52074 Aachen, Germany

3. Frédéric W. Patureau corresponding Aachen Institute of Organic Chemistry

   RWTH Aachen University

   Affiliation as printed

   Institute of Organic Chemistry RWTH Aachen University Landoltweg 1 52074 Aachen Germany

   Institute of Organic Chemistry, RWTH Aachen University, Landoltweg 1, 52074 Aachen, Germany