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A Modular and Scalable Route to Protected Cyclopropane Amino Acid Building Blocks

Year: 2025

Type: article

Abstract: High Resolution Image Download MS PowerPoint Slide An improved method for the synthesis of noncanonical cyclopropane amino acids from common laboratory reagents is described, avoiding the use of neurotoxic oxidants or precious metal catalysts. Intramolecular isocyanate trapping via a Hofmann rearrangement permits the synthesis of bicyclic carbamates in an enantioenriched and diastereopure manner. Subsequent ring-opening of these species allows access to cyclopropane amino acids which can be further functionalized via oxidation and S N 2 pathways and incorporated into peptides via solid-phase peptide synthesis.

Source: Organic Letters

DOI: 10.1021/acs.orglett.5c01341

Authors: Charlie T. Swan, Alex G. Edmonds, Stephen P. Argent, Nicholas J. Mitchell

Institution: University of Nottingham

Language: English

Topic: Cyclopropane Reaction Mechanisms

Subfield: Organic Chemistry

Field: Chemistry

Domain: Physical Sciences

Open Access status: hybrid

Estimated APC paid: $4,500

Funders: UK Research and Innovation, Leverhulme Trust, Engineering and Physical Sciences Research Council