Diastereoselective Synthesis of oxa‐Bridged Tetracyclic Benzooxazines from the Reaction of 2‐Isocyanophenyloxyacrylates and Propargylic Esters

A cascade annulation of 2‐isocyanophenyloxyacrylate and propargylic ester under basic conditions has been disclosed. This methodology enables diastereoselective synthesis of oxa‐bridged tetracyclic benzooxazine. The annulation proceeds through isomerization, Michael addition, triple annulation and a...

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Bibliographic Details
Published in:Advanced synthesis & catalysis 2021-08, Vol.363 (16), p.3957-3961
Main Authors: Xiao, Yao, Shen, Jie, Wang, Li, Lu, Shanya, Li, Jian
Format: Article
Language:English
Subjects:
2-Isocyanophenyloxyacrylate
Chemical reactions
Diastereoselective synthesis
Esters
Isomerization
Organic chemistry
Propargylic ester
Stereoselectivity
Tetracyclic benzooxazine
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Summary:A cascade annulation of 2‐isocyanophenyloxyacrylate and propargylic ester under basic conditions has been disclosed. This methodology enables diastereoselective synthesis of oxa‐bridged tetracyclic benzooxazine. The annulation proceeds through isomerization, Michael addition, triple annulation and acyl migration processes.
ISSN:1615-4150
1615-4169
DOI:10.1002/adsc.202100693