Asymmetric Synthesis of Spiro[Azetidine-3,3'-Indoline]-2,2'-Diones via Copper(I)-Catalyzed Kinugasa/C-C Coupling Cascade Reaction.

Angew Chem Int Ed Engl

International Cooperative Laboratory of Traditional Chinese Medicine Modernization and Innovative Drug Discovery of Chinese Ministry of Education (MOE), College of Pharmacy, Jinan University, No. 601 Huangpu Avenue West, Guangzhou, 510632, China.

Published: October 2022

AI Article Synopsis

  • - The text discusses the significance of spiro[azetidine-indolines] as key structures in various bioactive compounds.
  • - It highlights the current limitations in synthesizing a specific type of spiro[azetidine-indolines] and the unexplored area of chiral spiro[azetidine-3,3'-indolines].
  • - The work introduces a novel copper(I)-catalyzed reaction that enables an efficient and selective synthesis of chiral spiro[azetidine-3,3'-indoline]-2,2'-diones, marking a breakthrough in this area of research.

Article Abstract

Spiro[azetidine-indolines] are important scaffolds in diverse bioactive compounds. Current efforts to synthesize spiro[azetidine-indolines] are limited to chiral spiro[azetidine-2,3'-indolines]. Asymmetric synthesis of structurally similar chiral spiro[azetidine-3,3'-indolines] remains unexplored. In this work, the first copper(I)-catalyzed asymmetric Kinugasa/aryl C-C coupling cascade reaction is described. This provides a straightforward access to densely functionalized chiral spiro[azetidine-3,3'-indoline]-2,2'-diones in good yields and with high enantioselectivity.

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Source
http://dx.doi.org/10.1002/anie.202208323DOI Listing

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