ISSN:
0018-019X
Keywords:
Chemistry
;
Organic Chemistry
Source:
Wiley InterScience Backfile Collection 1832-2000
Topics:
Chemistry and Pharmacology
Notes:
Diastereo- and Enantioselective Reduction of beta;-Keto Esters Derived from Cyclopentanone, Cyclohexanone, Piperidone and Tetralone by ‘Non-fermenting’ Baker's YeastUnder ‘non-fermenting’ conditions, i.e. in tap water, in the absence of nutrients baker's yeast (25-380 g/g of substrate, aerobic) reduces β-keto esters such as those mentioned in the title with better selectivity than under the normally employed ‘fermenting’ conditions (sugar and nutrients, CO2 development). With the β- keto esters containing the tetralone substructure, large amount of yeast are required (250-380 g/g); the substrate disappears in the biomass, and the desired reduction product can be extracted after reaction times of up to a week at 30°. The configuration of most products(16-24) is established. Generally, the (R)-β-keto ester is reduced faster than the (S)-enantiomer (the two esters are in equilibrium under the reactio conditions), and the hydride transfer takes place preferentially from the diastereotopic Re-face. The β-hydroxy esters thus available are useful starting materials for syntheses of enantiomerically pure compounds (EPC).
Additional Material:
2 Ill.
Type of Medium:
Electronic Resource
URL:
http://dx.doi.org/10.1002/hlca.19870700618
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