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Updated: Aug 7, 2026

Enzymatic Cascade Reactions for the Synthesis of Chiral Amino Alcohols from L-lysine
Published on: February 16, 2018
Highly diastereoselective epimerization: stereodivergent synthesis of alpha-hydroxy-beta-amino isopentanoic acid
Woo Duck Seo1, Marcus J Curtis-Long, Young Bae Ryu
1Division of Applied Life Science (BK 21 Program), Department of Agricultural Chemistry, Research Institute of Life Science, Gyeongsang National University, 660-701, Korea.
Abstract:
The high diastereoselectivity of the base-catalyzed epimerization of oxazolidin-2-ones 7 and 8 is shown to depend on the nature of the N-substituent (R group); when R = Bn, the 4,5-trans-product (4S,5R)-9 is formed, whereas when R = H the 4,5-cis-product (4S,5S)-10 is formed, both with >99:1 dr. The successful hydrolysis of the oxazolidin-2-one group in both cis- and trans-derivatives show this to be a stereodivergent route to enantiopure alpha-hydroxy-beta-amino isopentanoic acids (2R,3S)-1 and (2S,3S)-2.
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