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Updated: Jun 4, 2025
Enzymatic Cascade Reactions for the Synthesis of Chiral Amino Alcohols from L-lysine
Published on: February 16, 2018
Electrochemical Oxidative Cascade Cyclization of Alkenyl Alcohols with External Nucleophiles to Access Amino- and
Liang-Chen Ren1, Min Wang1, Xiao Zha1
1Key Laboratory of Biocatalysis & Chiral Drug Synthesis of Guizhou Province, School of Pharmacy, Zunyi Medical University, Zunyi 563003, P. R. China.
Abstract:
A convenient electrochemical oxidative cascade cyclization of alkenes equipped with pendant alcohols with general nucleophiles was developed. Using readily available diarylmethanimine and carboxylic acids as nucleophilic sources, a broad range of internal alkene and terminal alkene substrates could produce RCO2- and Ar2CN-functionalized O-heterocycles in moderate to high yields without the requirement for external oxidants and metals. These resulting products can subsequently be hydrolyzed to yield valuable NH2- and OH-functionalized tetrahydrofurans and tetrahydropyranes under mild conditions. Importantly, the efficient conversion of secondary alcohol products to amines with complete inversion of configuration enhances the methodology, enabling the construction of 2-aryl-3-amino tetrahydrofuran with high and complementary diastereoselectivity.
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