Gold-Catalyzed Spirocyclization of Furan-ynones and Unexpected Skeleton Rearrangement of the Resulting Spirohydrofurans

被引：9

作者：

Chen, Yulong ^{[1
]}

Xu, Wei ^{[1
]}

Xie, Xin ^{[1
]}

Pei, Miaomiao ^{[1
]}

Lu, Mingduo ^{[1
]}

Wang, Yaotong ^{[1
]}

Liu, Yuanhong ^{[1
]}

机构：

[1] Chinese Acad Sci, Univ Chinese Acad Sci, Ctr Excellence Mol Synth, Shanghai Inst Organ Chem,State Key Lab Organometa, Shanghai 200032, Peoples R China

来源：

ORGANIC LETTERS | 2021年 / 23卷 / 03期

基金：

国家重点研发计划;

关键词：

D O I：

10.1021/acs.orglett.0c04312

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A gold-catalyzed cyclization of aniline-tethered furan-ynones has been developed. The reaction proceeds via trapping of the resulting stabilized cationic intermediate with an amide group leading to polycycles featured with a spiro-cyclohexadienone-hydrofuran framework with high efficiency. The resulting N-alkyl products undergo photorearrangements to afford the ring-enlarged benzo[b]azepine derivatives or iron-promoted novel rearrangement to diketone-containing spirocycles involving multiple C-X bond cleavages and formations.

引用

页码：1090 / 1095

页数：6

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