Aldehydes Switch Regioselectivity: a Prins Cyclization Strategy for the Synthesis of Indoline‐fused THFs and Indole‐fused Oxepanes

We have identified a switchable Prins cyclization process to form indoline‐fused tetrahydrofurans and indole‐fused oxepanes by applying different types of aldehydes under two sets of optimized conditions. Significantly, a novel Prins reaction mechanism involving an oxonium‐mediated rearrangement in...

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Bibliographic Details
Published in:Advanced synthesis & catalysis 2020-07, Vol.362 (13), p.2620-2625
Main Authors: Chen, Xiaobei, Jiang, Yuanrui, Geng, Huihui, Liu, Xingyu, Huang, Yizhuo, Lu, Jingwei, Gao, Chenjing, Zhang, Shilei, Zhang, Jian, Wang, Wei
Format: Article
Language:English
Subjects:
aldehyde
Aldehydes
Ethers
oxepane
Prins cyclization
Reaction mechanisms
rearrangement
Regioselectivity
tetrahydrofuran
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Summary:We have identified a switchable Prins cyclization process to form indoline‐fused tetrahydrofurans and indole‐fused oxepanes by applying different types of aldehydes under two sets of optimized conditions. Significantly, a novel Prins reaction mechanism involving an oxonium‐mediated rearrangement in the formation of five‐membered cyclic ethers is realized for the first time.
ISSN:1615-4150
1615-4169
DOI:10.1002/adsc.202000100