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Updated: Aug 26, 2026

Enzymatic Cascade Reactions for the Synthesis of Chiral Amino Alcohols from L-lysine
Published on: February 16, 2018
Fine-tuned aminal cleavage: a concise route to differentially protected enantiopure syn-alpha,beta-diamino Esters
Alma Viso1, Roberto Fernández de la Pradilla, María L López-Rodríguez
1Instituto de Química Orgánica, Consejo Superior de Investigaciones Científicas, Juan de la Cierva 3, E-28006 Madrid, Spain. iqov379@iqog.csic.es
Abstract:
A survey of routes for aminal cleavage of N-sulfinylimidazolidines has been carried out, and selective conditions to cleave the aminal moiety while preserving the sulfinamide group unaltered have been found. Thus, the treatment of enantiopure N-sulfinylimidazolidines with aqueous H(3)PO(4) in THF affords enantiopure N-sulfinyldiamino esters in excellent yields, while the presence of MeOH as cosolvent allows for the simultaneous removal of the sulfinamide group and aminal cleavage. The behavior of these substrates in a variety of chemical transformations has been explored.
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