European Journal of Organic Chemistry, volume 26, issue 25
A One‐Pot Approach to Multisubstituted Fused Aziridines: Formal Intermolecular [2+1] Cycloaddition Reaction between Saccharin‐Derived Cyclic Ketimines and Sulfur Ylides
Chao Lin
1, 2
,
Mao Chang Wang
1, 2
,
Peng Wie
1, 2
,
Qi Xing
1, 2
,
Chen He Liu
1, 2
1
Yantai Key Laboratory of Nanomedicine & Advanced Preparations Yantai Institute of Materia Medica Shandong 264000 P.R. China
|
2
Shandong Laboratory of Yantai Drug Discovery Bohai Rim Advanced Research Institute for Drug Discovery Yantai Shandong 264117 P.R. China
|
Publication type: Journal Article
Publication date: 2023-06-05
scimago Q2
SJR: 0.584
CiteScore: 5.4
Impact factor: 2.5
ISSN: 1434193X, 10990690
Organic Chemistry
Physical and Theoretical Chemistry
Abstract
Herein a concise and efficient method for the synthesis of aziridines has been developed. The reaction proceeds through a formal intermolecular [2+1] cycloaddition reaction of saccharin‐derived cyclic ketimines with sulfur ylides. This methodology features high atom‐economy, broad substrate scope and an operationally simple procedure, affording the aziridines with excellent yields and diastereoselectivity (>20 : 1 dr). In the presence of base, the aziridine products could be readily converted to benzothiazines by an unusual rearrangement reaction.
Found
Are you a researcher?
Create a profile to get free access to personal recommendations for colleagues and new articles.