Silver-Catalyzed Efficient Synthesis of Oxindoles and Pyrroloindolines via α-Aminoalkylation of N-Arylacrylamides with Amino Acid Derivatives

Kyalo Stephen Kanyiva; Sohei Makino; Takanori Shibata

doi:10.1002/asia.201701739

Silver-Catalyzed Efficient Synthesis of Oxindoles and Pyrroloindolines via α-Aminoalkylation of N-Arylacrylamides with Amino Acid Derivatives

Chem Asian J. 2018 Mar 2;13(5):496-499. doi: 10.1002/asia.201701739. Epub 2018 Jan 23.

Authors

Kyalo Stephen Kanyiva¹, Sohei Makino², Takanori Shibata²

Affiliations

¹ Global Center for Science and Engineering, School of Advanced Science and Engineering, Waseda University, Shinjuku, Tokyo, 169-8555, Japan.
² Department of Chemistry and Biochemistry, School of Advanced Science and Engineering, Waseda University, Shinjuku, Tokyo, 169-8555, Japan.

PMID: 29283517
DOI: 10.1002/asia.201701739

Abstract

α-Aminoalkylation of N-arylacrylamides with amino acid derivatives was achieved by silver-catalysis in moderate to high yields. The reaction provides an efficient strategy for the synthesis of functionalized oxindoles, and is suitable for a wide range of N-arylacrylamides and amino acids, both of which are inexpensive and readily available. The oxindoles obtained were readily transformed into densely functionalized pyrroloindolines by deprotection and cyclization in one pot.

Keywords: C−H activation; amino acids; aminoalkylation; oxindoles; pyrroloindolines; silver.