Catalyst‐Free Electrophilic Ring Expansion of  N ‐Unprotected Aziridines with  α ‐Oxoketenes to Efficient Access 2‐Alkylidene‐1,3‐Oxazolidines | Zendy

Chen Xingpeng | Zendy; Huang Zhengshuo | Zendy; Xu Jiaxi | Zendy

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Catalyst‐Free Electrophilic Ring Expansion of N ‐Unprotected Aziridines with α ‐Oxoketenes to Efficient Access 2‐Alkylidene‐1,3‐Oxazolidines

Author(s) -

Chen Xingpeng,

Huang Zhengshuo,

Xu Jiaxi

Publication year - 2021

Publication title -

advanced synthesis and catalysis

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 1.541

H-Index - 155

eISSN - 1615-4169

pISSN - 1615-4150

DOI - 10.1002/adsc.202100320

Subject(s) - chemistry , electrophile , ketene , ring (chemistry) , oxazolidine , catalysis , diazo , double bond , wolff rearrangement , medicinal chemistry , hydrogen bond , stereochemistry , polymer chemistry , organic chemistry , molecule

2‐(2‐Oxoalkylidene)‐1,3‐oxazolidine derivatives were synthesized in good to excellent yields regiospecifically through the catalyst‐free electrophilic ring expansion of N ‐unprotected aziridines and the ketene C=O double bond of α‐oxoketenes, in situ generated from the microwave‐assisted Wolff rearrangement of 2‐diazo‐1,3‐diketones. The ring expansion predominantly underwent an S N 1 process and the hydrogen bond decides the ( E )‐configuration of products.

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