Construction of 3‐Azabicyclo[3.1.0]hexane Backbone by the Reaction of Allenes with Allylamines via Tandem Michael Addition and Copper‐Mediated Oxidative Carbanion Cyclization. Issue 3 (5th February 2021)

• Record Type: Journal Article
• Authors: Xu, Hui; Han, Teng; Luo, Xiaoyan; Deng, Wei‐Ping
• Is Part Of: Chinese journal of chemistry. Volume 39:Issue 3(2021)
• Page Start: 666
• Page End: 670
• Publication Date: 2021-02-05
• Subjects: Oxidative coupling -- Allenes -- Allylamine -- 3‐Azabicyclo[3, 1, 0]hexane -- Miachel addition; Chemistry -- Periodicals; 540.5
• DOI: 10.1002/cjoc.202000405
• Languages: English
• ISSNs: 1001-604X

Abstract

Main observation and conclusion: A facile synthetic method for the construction of 3‐azabicyclo[3.1.0]hexane in the presence of copper catalyst system was developed. The reaction proceeds through Michael addition of allylamines with allenes followed by copper‐mediated intramolecular oxidative carbanion 5‐exo‐trig radical cyclization, affording potential biologically active 3‐azabicyclo[3.1.0]hexane derivatives in moderate to high yields (42%—85%). Abstract : Michael addition and copper‐mediated oxidative carbanion cyclization of allenes with allylamines was established, affording potential biologically active 3‐azabicyclo[3.1.0]hexane derivatives in moderate to high yields.