Synthesis of β-Amino Acids from α-Amino Acids Using Visible-Light Photoredox Catalysis

Keywords

β-amino acids - photoredox catalysis - phosphorus ylides - linchpins - deuteration - Wittig olefination - decarboxylative coupling

Significance

β-Amino acids (AAs) are essential building blocks for a wide range of biologically active molecules. The authors present an innovative two-step process that generates diverse β-AAs from α-AA derivatives and phosphonium ylides using visible-light photoredox catalysis. The ylides act as versatile bifunctional linchpins and generating carbon-centered radicals to access β-AAs with remarkable structural diversity.

Comment

Decarboxylative coupling of α-AA-derived N-hydroxyphthalimide (NHPI) esters with readily available phosphonium ylides occurs through a radical-polar crossover mechanism. The ylides act as both C-nucleophiles and sources of electrophilic radicals, facilitating a unique three-component assembly to access the β-AAs.

Publication History

Article published online:
25 February 2025