DBU-Promoted Tandem Cyclization of Ynones and Diazo Compounds: Direct Synthesis of Eight-Membered Cyclic Ethers

A novel DBU-promoted tandem cyclization reaction of ynones with diazo compounds as the N-terminal electrophiles has been developed. The reaction provides a simple and efficient method for the synthesis of fused eight-membered oxocino­[2,3-c] pyrazoles from readily available acyclic starting material...

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Bibliographic Details
Published in:Organic letters 2023-08, Vol.25 (31), p.5750-5755
Main Authors: Xu, Xue-Cen, Gong, Yue, Wang, Jie, Yuan, Yi-Rong, Zhao, Yu-Long
Format: Article
Language:English
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Summary:A novel DBU-promoted tandem cyclization reaction of ynones with diazo compounds as the N-terminal electrophiles has been developed. The reaction provides a simple and efficient method for the synthesis of fused eight-membered oxocino­[2,3-c] pyrazoles from readily available acyclic starting materials in a single step. This reaction allows the formation of four new bonds and two rings in a highly regio- and diastereoselective manner, where two adjacent stereocenters are created simultaneously in an atom-economic manner.
ISSN:1523-7060
1523-7052
DOI:10.1021/acs.orglett.3c01945