N-Oxide-Catalyzed Six-Membered Ring Bromo-Etherification of ϵ-Alkenyl Alcohols

被引：0
|
作者：
Hoshino, Yuki [1 ,2 ]
Kasahara, Honoka [1 ,2 ]
Marushima, Ryusei [1 ,2 ]
Moriyama, Katsuhiko [1 ,2 ]
机构：
[1] Chiba Univ, Grad Sch Sci, Dept Chem, 1-33 Yayoi Cho,Inage Ku, Chiba 2638522, Japan
[2] Chiba Univ, Soft Mol Activat Res Ctr, 1-33 Yayoi Cho,Inage Ku, Chiba 2638522, Japan
来源：
ADVANCED SYNTHESIS & CATALYSIS | 2025年 / 367卷 / 02期
关键词：
Bromo-etherification; Intramolecular cyclization; N-Oxide; Organocatalyst; Tetrahydropyran; OXA-MICHAEL REACTION; NATURAL-PRODUCTS; STEREOSELECTIVE CONSTRUCTION; PRINS CYCLIZATION; TETRAHYDROPYRANS; BROMOLACTONIZATION; BROMOCYCLIZATION; BROMINATION; MACROLIDES; STRATEGIES;
D O I：
10.1002/adsc.202401209
中图分类号：
O69 [应用化学];
学科分类号：
081704 ;
摘要：
A six-membered ring bromo-etherification of & varepsilon;-alkenyl alcohols using an N-oxide catalyst was developed to furnish 2-bromomethyl-6-substituted tetrahydropyrans with cis-selectivity and 3-bromomethyl isochromans in high yields. DFT calculations indicate that the NMO catalyst enhances the electrophilicity of the bromine atom on NBS via two hydrogen-bonding interactions after the formation of the NMO-NBS complex.
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页数：7
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