Phosphine-catalyzed [4+1] annulation of 1,3-(aza)dienes with maleimides: highly efficient construction of azaspiro[4.4]nonenes

Mei Yang; Tianyi Wang; Shixuan Cao; Zhengjie He

doi:10.1039/c4cc05624h

Phosphine-catalyzed [4+1] annulation of 1,3-(aza)dienes with maleimides: highly efficient construction of azaspiro[4.4]nonenes

Chem Commun (Camb). 2014 Nov 14;50(88):13506-9. doi: 10.1039/c4cc05624h.

Authors

Mei Yang¹, Tianyi Wang, Shixuan Cao, Zhengjie He

Affiliation

¹ The State Key Laboratory of Elemento-Organic Chemistry and Department of Chemistry, Nankai University and Collaborative Innovation Center of Chemical Science and Engineering (Tianjin), Tianjin 300071, P. R. China. zhengjiehe@nankai.edu.cn.

PMID: 25233907
DOI: 10.1039/c4cc05624h

Abstract

Phosphine-catalyzed [4+1] annulation of electron-deficient 1,3-dienes or 1,3-azadienes with maleimides has been successfully developed under very mild conditions, providing a convenient and highly efficient method for constructing 2-azaspiro[4.4]nonenes and 1,7-diazaspiro[4.4]nonenes. This reaction represents the first example of [4+1] cyclization between electron-deficient 4π-conjugated systems and non-allylic phosphorus ylides.

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Catalysis
Cycloaddition Reaction
Electrons
Maleimides / chemistry*
Phosphines / chemistry*
Spiro Compounds / chemical synthesis
Spiro Compounds / chemistry*

Substances

Maleimides
Phosphines
Spiro Compounds
phosphine