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Updated: Jan 6, 2026

Enzymatic Cascade Reactions for the Synthesis of Chiral Amino Alcohols from L-lysine
Published on: February 16, 2018
Synthesis of chiral lactams by asymmetric nitrogen insertion
Jasmin Hammes1, Clara Mañas1, Abhilash Pedada1
1Department Chemie, Johannes Gutenberg-Universität Duesbergweg 10-14 55128 Mainz Germany wahl@uni-mainz.de.
None:
Asymmetric nitrogen insertion into prochiral and meso cycloalkanones is achieved using diphenylphosphinyl hydroxylamine (DPPH) as the nitrogen source. A combination of Brønsted acid catalyst and Lewis acid promoter enables high yields and selectivity in the syntheses of a range of 5- to 7-membered lactams (19 examples, up to 97 : 3 er). Mechanistically, the sequence follows a Beckmann pathway involving an asymmetric condensation followed by a stereospecific rearrangement. The utility of the method is showcased by the syntheses of the drugs phenotropil, rolipram, pregabalin, and baclofen.
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