4.7 Article

Transition-metal-catalyzed switchable divergent cycloaddition of para-quinone methides and vinylethylene carbonates: Access to different sized medium-sized heterocycles

Journal

CHINESE CHEMICAL LETTERS
Volume 33, Issue 10, Pages 4549-4558

Publisher

ELSEVIER SCIENCE INC
DOI: 10.1016/j.cclet.2022.01.063

Keywords

Medium-sized rings; Divergent cycloaddition; Regioselectivity; para-Quinone methides; Vinylethylene carbonates

Funding

  1. National Natural Science Foundation of China [82173664, 81803342]
  2. ShuangChuang Research Team of Jiangsu Province [20182036]
  3. King Abdullah University of Science and Technology (KAUST)

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This study developed a divergent synthesis method for medium-sized rings with controllable ring sizes, successfully synthesizing seven- to ten-membered nitrogen-containing heterocycles. The method features operational simplicity, broad substrate scope, and excellent regioselectivity.
Divergent synthesis of medium-sized rings with controllable ring sizes represents a longstanding challenge in organic synthesis. Herein, we developed a transition-metal-catalyzed switchable divergent cycloaddition of para-quinone methides and vinylethylene carbonates by controlling the steric hindrance of substituent. Different from reported alkoxide-triggered annulations, this process undergoes a regiodivergent allylation of para-quinone methides followed by 1,6-addition reaction, providing a new route to selectively synthesize seven- to ten-membered nitrogen-containing heterocycles in high yields with excellent regioselectivities. This protocol features a broad substrate scope, wide functional group tolerance as well as operational simplicity. The reaction mechanism was investigated by conducting a series of control experiments as well as DFT calculations and the origins of the regioselectivities of the cycloaddition process were rationalized. (C) 2022 Published by Elsevier B.V. on behalf of Chinese Chemical Society and Institute of Materia Medica, Chinese Academy of Medical Sciences.

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