Biocatalytic Approaches towards the Synthesis of Chiral Amino Alcohols from Lysine: Cascade Reactions Combining alpha‐Keto Acid Oxygenase Hydroxylation with Pyridoxal Phosphate‐ Dependent Decarboxylation

Amino alcohols are a very common structural motif in natural and synthetic molecules. Starting from l‐lysine and hydroxy‐l‐lysine, a straightforward biocatalytic synthesis of beta‐ and gamma‐amino alcohols is presented. Diastereoselective C–H oxidation catalyzed by an alpha‐keto acid‐dependent oxygenase followed by cleavage of the carboxylic acid moiety of the corresponding chiral hydroxy amino acid by a pyridoxal phosphate‐dependent decarboxylase enabled the formation of the target amino alcohols with moderate to complete conversions. Four beta‐ and gamma‐amino alcohols were obtained on a small scale in excellent yields and stereoselectivities.