Chemo- and Stereoselective Reduction of β-Keto-α-oximino Nitriles by Using Baker's Yeast
- Chemo- and Stereoselective Reduction of β-Keto-α-oximino Nitriles by Using Baker's Yeast
- 모길웅; 강순방; 김유승; 이용섭; 이재욱; 금교창
- synthetic methods; biotransformations; reduction; chemoselectivity; enantioselectivity
- Issue Date
- European journal of organic chemistry
- VOL 2015, NO 5, 1137-1143
- The baker’s yeast mediated reduction of β-keto-α-oximino nitriles 3 at 20 °C gave β-hydroxy-α-oximino nitriles 4 in high yields with high enantiomeric purity [enantiomeric excess (ee) values 99%]. At room temperature, the same reaction afforded the product in a slightly lower yield. The β-hydroxy-α-oximino nitriles 4 were obtained as single stereoisomers according to chiral GC–MS analyses and the 1H and 19F NMR spectra of the corresponding Mosher esters. The abso-
lute stereochemistry of alcohol 4a was determined by hydrolysis of its oximino nitrile group followed by conversion into its corresponding α-hydroxy ester. The β-hydroxy-α-oximino nitrile products were further submitted to oxime- and nitrileselective transformations. This chemo- and stereoselective reduction can be used to generate important chiral building blocks.
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