Enantioselective Synthesis of Aminodiols by Sequential Rhodium-Catalysed Oxyamination/Kinetic Resolution: Expanding the Substrate Scope of Amidine-Based Catalysis

Regio‐ and stereoselective oxyamination of dienes through a tandem rhodium‐catalysed aziridination–nucleophilic opening affords racemic oxazolidinone derivatives, which undergo a kinetic resolution acylation process with amidine‐based catalysts (ABCs) to achieve s values of up to 117. This protocol was applied to the enantioselective synthesis of sphingosine.

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J. Guasch; I. Gimenez-Nueno; I. Funes-Ardoiz; M. Bernus; M. I. Matheu; F. Maseras; S. Castillon; Y. Diaz

CHEM-EUR J 2018, 24 (18), 4635-4642
DOI: 10.1002/chem.201705670

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