Stereoselective Formation of Bis(α-hydroxy ketones) via Enzymatic Carboligation

Stereoselective Formation of Bis(α-hydroxy ketones) via Enzymatic Carboligation

The enzymatic approach to a novel class of chiral bis(α-hydroxy ketones) of type 5 and 8, which enable the synthesis of new multidentate ligands for asymmetric transition metal catalysis, is described. The key step is the second benzoylformate decarboxylase catalyzed C−C-bond formation between an ar...

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Veröffentlicht in:Journal of organic chemistry 2000-12, Vol.65 (25), p.8608-8612
Hauptverfasser: Dünnwald, Thomas, Müller, Michael
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container_title Journal of organic chemistry
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creator Dünnwald, Thomas
Müller, Michael
description The enzymatic approach to a novel class of chiral bis(α-hydroxy ketones) of type 5 and 8, which enable the synthesis of new multidentate ligands for asymmetric transition metal catalysis, is described. The key step is the second benzoylformate decarboxylase catalyzed C−C-bond formation between an aromatic dialdehyde and acetaldehyde, which proceeds with complete stereocontrol. Transformation of enantiomerically enriched monoadduct (S)-4 (ee 88%) and (S)-7 (ee 79%) resulted in optical pure (S,S)-5 and (S,S)-8 besides minor amounts of the corresponding diastereomeric meso-forms.
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title Stereoselective Formation of Bis(α-hydroxy ketones) via Enzymatic Carboligation
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