Enantioselective Cycloaddition of in Situ Formed aza-Dienes and Vinyl Diazo Compounds for the Synthesis of Optically Enriched and Diazo Containing Tetrahydropyridazine

A copper catalyzed enantioselective formal aza-Diels–Alder reaction of in situ formed 1,2-diaza-1,3-dienes from α-halohydrazones and vinyl diazo compounds was described. The protocol provides a variety of optically enriched diazo-containing tetrahydropyridazines in moderate yields and with up to exc...

Full description

Saved in:
Bibliographic Details
Published in:Journal of organic chemistry 2024-12, Vol.89 (24), p.18752-18758
Main Authors: Li, Song-Liang, Yang, Ting, Yin, Yi-Xiao, Karmaker, Pran Gopal, Chu, Wen-Dao, Zhou, Qing, Liu, Quan-Zhong
Format: Article
Language:English
Online Access:Get full text
Tags: Add Tag
No Tags, Be the first to tag this record!
Description
Summary:A copper catalyzed enantioselective formal aza-Diels–Alder reaction of in situ formed 1,2-diaza-1,3-dienes from α-halohydrazones and vinyl diazo compounds was described. The protocol provides a variety of optically enriched diazo-containing tetrahydropyridazines in moderate yields and with up to excellent enantioselectivities. The present methodologies utilize chiral oxazolines as the chiral ligands for asymmetric catalysis and feature mild reaction conditions, readily available substrates, and broad substrate scope.
ISSN:0022-3263
1520-6904
1520-6904
DOI:10.1021/acs.joc.4c02499