Diastereo- and Enantioselective Palladium-Catalyzed Dearomative [3+2] Cycloaddition of 3-Nitroindoles

Jia-Jia Suo; Wei Liu; Juan Du; Chang-Hua Ding; Xue-Long Hou

doi:10.1002/asia.201800133

Diastereo- and Enantioselective Palladium-Catalyzed Dearomative [3+2] Cycloaddition of 3-Nitroindoles

Chem Asian J. 2018 Apr 16;13(8):959-963. doi: 10.1002/asia.201800133. Epub 2018 Mar 23.

Authors

Jia-Jia Suo^{1

2}, Wei Liu¹, Juan Du^{1

2}, Chang-Hua Ding¹, Xue-Long Hou^{1

3}

Affiliations

¹ State Key Laboratory of Organometallic Chemistry, Center for Excellence in Molecular Synthesis, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 345 Lingling Road, Shanghai, 200032, China.
² University of Chinese Academy of Sciences, Beijing, China.
³ Shanghai-Hong Kong Joint Laboratory in Chemical Synthesis, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences., China.

PMID: 29570935
DOI: 10.1002/asia.201800133

Abstract

Diastereo- and enantioselective cycloaddition of 3-nitroindoles with vinyl aziridine was realized under Pd-catalysis using commercially available Walphos as the ligand, affording pyrroloindolines in high yields with high diastereo- and enantioselectivities. The reaction can be scaled up to a gram scale and the reaction products are easily converted to amino pyrroloindoline and other pyrroloindoline derivatives.

Keywords: [3+2] cycloaddition; asymmetric catalysis; dearomatization; nitroindoles; palladium.