This title appears in the Scientific Report :
2000
Please use the identifier:
http://dx.doi.org/10.1021/jo0010274 in citations.
Please use the identifier: http://hdl.handle.net/2128/719 in citations.
Stereoselective formation of Bis(alpha-hydroxy-ketones) via enzymatic carboligation
Stereoselective formation of Bis(alpha-hydroxy-ketones) via enzymatic carboligation
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 a...
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Personal Name(s): | Dünnwald, T. |
---|---|
Müller, M. | |
Contributing Institute: |
Institut für Biotechnologie; IBT |
Published in: | The @journal of organic chemistry, 65 (2000) S. 8608 - 8612 |
Imprint: |
[S.l.]
American Chemical Society
2000
|
Physical Description: |
8608 - 8612 |
DOI: |
10.1021/jo0010274 |
PubMed ID: |
11112581 |
Document Type: |
Journal Article |
Research Program: |
Verfahrenstechnik zur mikrobiellen Gewinnung von Primärmetaboliten |
Series Title: |
Journal of Organic Chemistry
65 |
Subject (ZB): | |
Link: |
OpenAccess |
Publikationsportal JuSER |
Please use the identifier: http://hdl.handle.net/2128/719 in citations.
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. |