Lewis-Base-Catalyzed Enantioselective Formal [4 + 2] Annulations of Morita-Baylis-Hillman Carbonates: Access to Tetrahydroquinolines Derivatives.

Org Lett

State Key Laboratory and Institute of Elemento-Organic Chemistry, College of Chemistry, Nankai University, Tianjin 300071, China.

Published: May 2023

AI Article Synopsis

  • A new chemical reaction has been developed that uses a Lewis base to create a specific type of compound through a formal [4 + 2] annulation process.
  • The reaction combines acylamino-aryl MBH carbonates with electron-deficient olefins, resulting in the formation of tetrahydroquinolines.
  • These tetrahydroquinolines have three stereogenic centers, including a quaternary stereocenter, and are produced in high yields with good enantioselectivity.

Article Abstract

The Lewis-base-catalyzed enantioselective formal [4 + 2] annulation reaction of -acylamino-aryl MBH carbonates and electron-deficient olefins was developed. Tetrahydroquinolines with three sequential stereogenic centers containing a quaternary stereocenter were obtained in high yields with good enantioselectivity.

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Source
http://dx.doi.org/10.1021/acs.orglett.3c00525DOI Listing

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