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. 2018 Mar 26;24(18):4635-4642.
doi: 10.1002/chem.201705670. Epub 2018 Feb 28.

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

Joan Guasch  1 , Irene Giménez-Nueno  1 , Ignacio Funes-Ardoiz  2 , Miguel Bernús  1 , M Isabel Matheu  1 , Feliu Maseras  2   3 , Sergio Castillón  1 , Yolanda Díaz  1
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Enantioselective Synthesis of Aminodiols by Sequential Rhodium-Catalysed Oxyamination/Kinetic Resolution: Expanding the Substrate Scope of Amidine-Based Catalysis

Joan Guasch et al. Chemistry. .

Abstract

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.

Keywords: enantioselectivity; kinetic resolution; organocatalysis; oxyamination; synthesis design.

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