Details

Autor(en) / Beteiligte

• Mou, Xue-Qing
• Wang, Min
• Ren, Liang-Chen
• Jian, Yu-Rui
• Fu, Xin-Yu
• Zheng, Hong-Yu
• Zha, Xiao
• Cui, Bao-Dong
• Zhang, Yun
• Chen, Yong-Zheng

Titel

Photoredox-catalyzed intramolecular oxy- and aminoacylation of alkenes with acyl oxime esters: facile synthesis of acylated saturated heterocycles

Ist Teil von

• Organic Chemistry Frontiers, 2023-12, Vol.11 (1), p.74-82

Ort / Verlag

London: Royal Society of Chemistry

Erscheinungsjahr

2023

Quelle

Alma/SFX Local Collection

Beschreibungen/Notizen

• In the present paper, an efficient photoredox-catalyzed intramolecular oxy- and aminoacylation of internal alkenes equipped with pendant oxygen- or nitrogen-centered nucleophiles with acyl oxime esters is reported. Under visible-light irradiation, a variety of structurally diverse acylated saturated heterocycles, such as tetrahydrofurans, tetrahydropyrans, δ-valerolactones, tetrahydropyrroles, piperidines, tetrahydro-1,3-oxazepines, etc ., were efficiently synthesized from easily accessible unsaturated alcohols, carboxylic acids, tosyl-protected amines, and O -homoallyl benzimidates via an acyl radical-mediated cascade acylation/cyclization process. This light-driven transformation features a broad substrate scope, good functional group compatibility, high regio- and diastereoselectivity, and mild reaction conditions, representing a general and practical procedure toward the construction of acylated saturated heterocycles as well as their derivatives.