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Updated: Feb 25, 2026

Preparation of Enantiopure Non-Activated Aziridines and Synthesis of Biemamide B, D, and epiallo-Isomuscarine
Published on: June 13, 2022
Diastereoselective Cyclopropanation with Secondary Diazoacetamides to Access
Terrence-Thang H Nguyen1, Takeru Saito1, Warren Chang1
1Department of Chemistry, Emory University, Atlanta, Georgia 30322, United States.
None:
A dirhodium(II) tetracarboxylate-catalyzed reaction of secondary diazoacetamides with N-Boc-2,5-dihydro-1H-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.
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