Diastereoselective Cyclopropanation with Secondary Diazoacetamides to Access endo -Azabicyclo[3.1.0]hexane-6-carboxamides

Organic Letters 2026 Open access

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Authors: Terrence-Thang H. Nguyen, Takeru Saito, Warren Chang, Antonio Navarro, Huw M. L. Davies
DOI: 10.1021/acs.orglett.6c00392
Cited by: 3
References: 22

Abstract

High Resolution Image Download MS PowerPoint Slide A dirhodium(II) tetracarboxylate-catalyzed reaction of secondary diazoacetamides with N -Boc-2,5-dihydro-1 H -pyrrole results in a highly diastereoselective cyclopropanation for the synthesis of endo -azabicyclo[3.1.0]hexane-6-carboxamides. These reaction conditions work well for secondary diazoacetamides but are not compatible with their tertiary amide counterparts. A base-mediated equilibration of the endo -isomer allows access to the exo -azabicyclo[3.1.0]hexane-6-carboxamides. The utility of this cyclopropanation chemistry was illustrated by its application to the synthesis of the drug candidate, Mazisotine.

Fields of Study & Subjects

Cyclopropane Reaction Mechanisms Radical Photochemical Reactions Synthesis and Catalytic Reactions

Publication details

Journal / source
Organic Letters
Publisher
American Chemical Society (ACS)
Volume
28
Issue
9
Pages
3063–3067
Publication date
23 February 2026
Language
EN