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Please login to access the full content or check if you have access via Variation 2: β-Amino Acid Derivatives by the Arndt–Eistert Reaction

DOI: 10.1055/sos-SD-023-00535

Tidwell, T. T.Science of Synthesis, (200623593.

ArndtEistert chain elongation of α-amino acids through the Wolff rearrangement has wide applications in the preparation of β-amino acid derivatives used as precursors of nonnatural peptides.[‌104‌,‌105‌] The reaction of the diazo ketones 143, derived from a diverse group of α-amino acids, proceeds with complete retention of the stereochemistry of the diazo ketones in the product esters 145 (Scheme 45).[‌104‌,‌105‌] The ketenes 144 that are formed also undergo selective reactions with particular hydroxy groups of polyfunctional substrates.[‌105‌]

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