Synthesis of 3-azabicyclo[3.1.0]hexane derivatives via palladium-catalyzed cyclopropanation of maleimides with N-tosylhydrazones: practical and facile access to CP-866,087?

Organic & Biomolecular Chemistry Pub Date: 2017-01-05 DOI: 10.1039/C6OB02137A

Abstract

A palladium-catalyzed cyclopropanation of internal alkenes with N-tosylhydrazones is presented. This gram-scale cyclopropanation reaction of maleimides provides a wide spectrum of 3-azabicyclo[3.1.0]hexane derivatives in high yields and diastereoselectivities. The major diastereoisomers could be easily isolated by chromatography on silica gel. This protocol provides a practical route to the mu opioid receptor antagonist CP-866,087.

Graphical abstract: Synthesis of 3-azabicyclo[3.1.0]hexane derivatives via palladium-catalyzed cyclopropanation of maleimides with N-tosylhydrazones: practical and facile access to CP-866,087
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