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Regioselective access to polycyclic N-heterocycles via homogeneous copper-catalyzed cascade cyclization of allenynes

Authors :
Kua-Fei Wei
Qing Liu
Guang Ma
Xiao-Lei Jiang
Xiu-Hong Zhu
Guang-Xin Ru
Wen-Bo Shen
Source :
Communications Chemistry, Vol 6, Iss 1, Pp 1-9 (2023)
Publication Year :
2023
Publisher :
Nature Portfolio, 2023.

Abstract

Abstract Polycyclic N-heterocycles are important structural motifs commonly found in bioactive compounds, however, their selective construction via the cyclization of allenynes remains challenging yet highly desirable. Here we show a homogeneous copper-catalyzed hetero Diels−Alder (HDA) reaction of allenynes with cis-diazenes (PTAD, 4-phenyl-1,2,4-triazoline-3,5-dione), allowing the practical and efficient synthesis of a diverse array of valuable polycyclic N-heterocycles. A temperature-controlled and stereocontrolled chemoselectivity of the reaction was observed, leading to the chemodivergent synthesis of tetracyclic pyrrolidines, pentacyclic triazepanes and tricyclic pyrrolidines. Compared with related Au-catalyzed cyclization of allenynes, this copper catalysis achieves cyclization of allenynes terminating in C–N bond formation via the HDA reaction.

Subjects

Subjects :
Chemistry
QD1-999

Details

Language :
English
ISSN :
23993669
Volume :
6
Issue :
1
Database :
Directory of Open Access Journals
Journal :
Communications Chemistry
Publication Type :
Academic Journal
Accession number :
edsdoj.6a204051496347a68c1ece37d63cc410
Document Type :
article
Full Text :
https://doi.org/10.1038/s42004-023-00910-9