Up-scale pseudo-telescopic photo-induced Arndt-Eistert α-amino acids homologation in flow reactors cascade

09 January 2024, Version 1
This content is a preprint and has not undergone peer review at the time of posting.


We present an efficient, pseudo-telescopic synthesis of β-amino acids via the Arndt Eistert homologation of α-amino acids using flow reactors cascade. Our system utilizes flow generation of diazomethane, diazoketone preparation, and subsequent photo-flow Wolff rearrangement without intermediate isolation. This innovative method enhances safety, improves scalability, and allows access to substrates previously unavailable in the thermal/catalytic Wolff rearrangement. Notably, the reaction conditions are mild, which leads to high yields and excellent purity, thereby expanding the synthetic utility of the Wolff rearrangement. This work unveils a versatile and scalable approach in β-amino acid synthesis, opening new avenues in synthetic and medicinal chemistry.


flow reactor
Arndt-Eistert homologation
α-protected amino acids
β-amino acids

Supplementary materials

Supporting Information
1. Laboratory scale photo flow setup details 2. Pilot scale flow setup details 3. Experimental Details 4. Representative set, for chromatographic ee determination for starting and homologated amino acids 5. Optical purity summary for starting (if available) and homologated amino acids, experimental data 6. List of methods used for chiral analysis and experimental details for these methods


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