Stereoselective Formation of Bis(α-hydroxy ketones) via Enzymatic Carboligation
- 21 November 2000
- journal article
- research article
- Published by American Chemical Society (ACS) in The Journal of Organic Chemistry
- Vol. 65 (25) , 8608-8612
- https://doi.org/10.1021/jo0010274
Abstract
The enzymatic approach to a novel class of chiral bis(alpha -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.This publication has 13 references indexed in Scilit:
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