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Updated: Jan 27, 2026

Enzymatic Cascade Reactions for the Synthesis of Chiral Amino Alcohols from L-lysine
Published on: February 16, 2018
1,2-Amino Alcohols via Visible-Light-Mediated Mannich-Type Reaction Enabled by Brook Rearrangement
Ai-Lian Wang1, Yi-Fan Yao1, Xu-Gang Zhang2
1State Key Laboratory of Natural Product Chemistry, College of Chemistry and Chemical Engineering, Lanzhou University, Lanzhou 730000, Gansu, China.
Abstract:
Herein, we report a catalyst-free, photosensitized strategy for synthesizing 1,2-amino alcohols. This transformation proceeds via the addition of an α-hydroxymethyl radical to an in situ-generated alkyliminium ion. The α-hydroxymethyl radical is formed by the radical Brook rearrangement of a (trimethylsilyl)methoxy radical generated from an electron donor-acceptor (EDA) complex between Hantzsch ester and N-((trimethylsilyl)methoxy)phthalimide. Therefore, this Mannich-type reaction establishes an additive-free, modular, and simple approach for the synthesis of 1,2-amino alcohols.
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