Recent Developments in Azomethine Ylide-Initiated Double Cycloadditions
Tieli Zhou, Xiaofeng Zhang, Yan Jan Sheng, Desheng Zhan, Wei Zhang
TL;DR
This paper reviews recent advances in using azomethine ylides for efficient synthesis of complex heterocyclic compounds.
Contribution
The paper introduces a PASE method to improve the efficiency of double cycloadditions using azomethine ylides.
Findings
AMYs are effective 1,3-dipoles for [3+2] cycloadditions in pyrrolidine synthesis.
Double cycloadditions enable the creation of novel polyheterocyclic structures.
The PASE method enhances reaction efficiency and green chemistry principles.
Abstract
Azomethine ylides (AMYs) have a nitrogen–carbon double bond and an electron lone pair on the nitrogen atom. They are essential 1,3-dipoles for [3+2] cycloadditions in the synthesis of pyrrolidine-containing heterocycles. Significant progress in 1,3-diplolar cycloadditions has been made in the construction of novel heterocyclic scaffolds, with efforts to broaden substrate scope, enhance stereoselectivity, and integrate green chemistry principles. This article summarizes double cycloadditions of AMYs derived from amino esters and amino acids for the synthesis of novel polyheterocycles. The design of double cycloadditions through the pot, atom, and step economic (PASE) method to increase the reaction efficiency is discussed. The examples presented in this paper may be applied to the synthesis of biologically active molecules.
Genes, proteins, chemicals, diseases, species, mutations and cell lines named across the full text — each resolved to its canonical identifier and authoritative record.
Click any figure to enlarge with its caption.
Figure 1
Figure 2
Figure 3
Figure 4
Figure 5
Figure 6
Figure 7
Figure 8
Figure 9
Figure 10
Figure 11
Figure 12
Figure 13
Figure 14
Figure 15
Figure 16
Figure 17
Figure 18
Figure 19
Figure 20
Figure 21
Figure 22
Figure 23
Figure 24
Figure 25
Figure 26
Figure 27Peer Reviews
No public reviews on file for this paper yet. If you reviewed it on a platform where reviews are public (OpenReview, ICLR, NeurIPS, ICML), you can paste yours below so the community can read it here.
Videos
No videos yet. Explain this paper in a talk, walkthrough, or lecture? Add one.
Taxonomy
TopicsSynthesis and Catalytic Reactions · Cyclopropane Reaction Mechanisms · Synthesis of β-Lactam Compounds