Qiu H,
Matsumoto A *,
Maruoka K *.
Kyoto University, Japan and Guangdong University of Technology, Guangzhou, P. R. China
Sequential Photocatalysis for Homologative Diversification of α-Amino Acids to β-Amino
Acids via Phosphonium Ylide Linchpin Strategy.
J. Am. Chem. Soc. 2024;
146: 35478-35485
DOI:
10.1021/jacs.4c14860
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.
