2008•Organic LettersRequires access

Enantiopure 1,5-Diols from Dynamic Kinetic Asymmetric Transformation. Useful Synthetic Intermediates for the Preparation of Chiral Heterocycles

Karin Leijondahl, Linnéa Borén, Roland U. Braun, Jan‐E. Bäckvall

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Abstract

Dynamic kinetic asymmetric transformation (DYKAT) of a series of 1,5-diols has been performed in the presence of Candida antarctica lipase B (CALB), Pseudomonas cepacia lipase II (PS-C II), and ruthenium catalyst 4. The resulting optically pure 1,5-diacetates are useful synthetic intermediates, which was demonstrated by the syntheses of both an enantiopure 2,6-disubstituted piperidine and an enantiopure 3,5-disubstituted morpholine.

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What this paper is about

Dynamic kinetic asymmetric transformation (DYKAT) of a series of 1,5-diols has been performed in the presence of Candida antarctica lipase B (CALB), Pseudomonas cepacia lipase II (PS-C II), and ruthenium catalyst 4. The resulting optically pure 1,5-diacetates are useful synthetic intermediates, which was demonstrated by the syntheses of both an enantiopure 2,6-disubstituted piperidine and an enantiopure 3,5-disubstituted morpholine.

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Available abstract

Dynamic kinetic asymmetric transformation (DYKAT) of a series of 1,5-diols has been performed in the presence of Candida antarctica lipase B (CALB), Pseudomonas cepacia lipase II (PS-C II), and ruthenium catalyst 4. The resulting optically pure 1,5-diacetates are useful synthetic intermediates, which was demonstrated by the syntheses of both an enantiopure 2,6-disubstituted piperidine and an enantiopure 3,5-disubstituted morpholine.

Key concepts: Enantiopure drug, Candida antarctica, Chemistry, Morpholine, Kinetic resolution, Piperidine, Lipase, Ruthenium

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Enantiopure 1,5-Diols from Dynamic Kinetic Asymmetric Transformation. Useful Synthetic Intermediates for the Preparation of Chiral Heterocycles — Research Paper | ScholarLens