Regioselective Aryne Annulations of N-Tosyl-2-enamides and N-tert-Butylsulfinyl-2-enamides for the Construction of Dihydroquinolin-4-one and Chroman-4-imine Units DOI
Aimin Zhang,

Suh Young Yu,

Jihye Lee

et al.

Organic Letters, Journal Year: 2025, Volume and Issue: unknown

Published: Feb. 14, 2025

A regioselective synthesis of the dihydroquinolin-4-one 4 is achieved from aryne-mediated annulation an o-(trimethylsilyl)aryl triflate 1 with N-tosyl-2-enamide 2 in presence TBAT toluene, whereas chroman-4-imine 5 formed reaction N-(tert-butylsulfinyl)-2-enamide 3 and TBAF THF. Governing factors for regioselectivity have been accounted as strong steric electronic effects between N-toluenesulfonyl N-tert-butylsulfinyl groups 3. The methods described herein are successful various substrates or high levels regioselectivity, diastereoselectivity 5.

Language: Английский

Regioselective Aryne Annulations of N-Tosyl-2-enamides and N-tert-Butylsulfinyl-2-enamides for the Construction of Dihydroquinolin-4-one and Chroman-4-imine Units DOI
Aimin Zhang,

Suh Young Yu,

Jihye Lee

et al.

Organic Letters, Journal Year: 2025, Volume and Issue: unknown

Published: Feb. 14, 2025

A regioselective synthesis of the dihydroquinolin-4-one 4 is achieved from aryne-mediated annulation an o-(trimethylsilyl)aryl triflate 1 with N-tosyl-2-enamide 2 in presence TBAT toluene, whereas chroman-4-imine 5 formed reaction N-(tert-butylsulfinyl)-2-enamide 3 and TBAF THF. Governing factors for regioselectivity have been accounted as strong steric electronic effects between N-toluenesulfonyl N-tert-butylsulfinyl groups 3. The methods described herein are successful various substrates or high levels regioselectivity, diastereoselectivity 5.

Language: Английский

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