Premium
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.