This title appears in the Scientific Report :
2018
Please use the identifier:
http://dx.doi.org/10.1002/cctc.201801040 in citations.
Enantioselective, Catalytic One‐Pot Synthesis of γ‐Butyrolactone‐Based Fragrances
Enantioselective, Catalytic One‐Pot Synthesis of γ‐Butyrolactone‐Based Fragrances
Herein the preparative (1 g scale), stereoselective syntheses of various alkyl‐substituted γ‐butyrolactone fragrances 1 is described. The α,β‐unsaturated γ‐keto esters 2 as starting materials were synthesized by a Horner‐Wadsworth‐Emmons reaction and are further reduced by an ene reductase and alcoh...
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Personal Name(s): | Kumru, Ceyda |
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Classen, Thomas / Pietruszka, Jörg (Corresponding author) | |
Contributing Institute: |
Biotechnologie; IBG-1 Institut für Bioorganische Chemie (HHUD); IBOC |
Published in: | ChemCatChem, 10 (2018) 21, S. 4917-4926 |
Imprint: |
Weinheim
WILEY-VCH Verlag
2018
|
DOI: |
10.1002/cctc.201801040 |
Document Type: |
Journal Article |
Research Program: |
Biotechnology |
Publikationsportal JuSER |
Herein the preparative (1 g scale), stereoselective syntheses of various alkyl‐substituted γ‐butyrolactone fragrances 1 is described. The α,β‐unsaturated γ‐keto esters 2 as starting materials were synthesized by a Horner‐Wadsworth‐Emmons reaction and are further reduced by an ene reductase and alcohol dehydrogenase in a one‐pot enzyme cascade to nine desired γ‐butyrolactones 1, among them whisky (1 c) and cognac lactone (1 d). The products 1 were obtained in moderate to good yields and very good diastereoselectivities. Furthermore, the position of a nBu‐substituent was permutated to study the effect on the enzyme cascade. |