Phosphine-Catalyzed Chemoselective [4+3] Cycloaddition of Alminine Esters and β′-acetoxy Allenoates for Divergent Synthesis of Azepines

被引：40

作者：

Dai, Zonghao ^{[1
]}

Zhu, Jin ^{[1
]}

Wang, Jiahua ^{[1
]}

Su, Wenbo ^{[1
]}

Yang, Fulai ^{[1
]}

Zhou, Qingfa ^{[1
]}

机构：

[1] China Pharmaceut Univ, Dept Organ Chem, State Key Lab Nat Med, Nanjing 210009, Jiangsu, Peoples R China

来源：

ADVANCED SYNTHESIS & CATALYSIS | 2020年 / 362卷 / 03期

基金：

中国国家自然科学基金;

关键词：

phosphine; azepines; cycloaddition; aldimine esters; allenoates; FORMAL 3+2+2 CYCLOADDITION; RING-CLOSING METATHESIS; FACILE SYNTHESIS; ANNULATION; ALKYNES; IMINES; GENERATION; ALLENES; ACCESS; 1,2,3-TRIAZOLES;

D O I：

10.1002/adsc.201901132

中图分类号：

O69 [应用化学];

学科分类号：

081704 ;

摘要：

Text. A general method for the synthesis of structural diversity and complexity of azepines from aldimine esters and beta '-acetoxy allenoates is reported. Under phosphine catalysis, a [4+3] cycloaddition for the formation of 1,3-dihydro-2H-azepine-2,2,4-tricarboxylates was achieved with broad substrate scope under mild reactions. A switchable process was given and a variety of important 2,3-dihydrochromeno[4,3-b]azepin-6(1H)-ones were selectively formed when the reaction was performed in the presence of Cs2CO3 and PPh3, which involved an intramolecular ester group migration and subsequent lactonization of 1,3-dihydro-2H-azepine-2,2,4-tricarboxylates. Besides easy handle process, high synthetic value of resulting products, it is worth to note that this work showed the novel example of 1,5-ethoxycarbonyl migration.

引用

页码：545 / 551

页数：7

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