Journal
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
Volume 2015, Issue 5, Pages 1137-1143Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/ejoc.201403393
Keywords
Synthetic methods; Biotransformations; Reduction; Chemoselectivity; Enantioselectivity
Categories
Funding
- Korea Institute of Science and Technology Institutional Program [2E25023, 2Z03983]
- National Research Council of Science & Technology (NST), Republic of Korea [2E25023] Funding Source: Korea Institute of Science & Technology Information (KISTI), National Science & Technology Information Service (NTIS)
Ask authors/readers for more resources
The baker's yeast mediated reduction of beta-keto-alpha-oximino nitriles 3 at 20 degrees C gave beta-hydroxy-alpha-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 beta-hydroxy-alpha-oximino nitriles 4 were obtained as single stereoisomers according to chiral GC-MS analyses and the H-1 and F-19 NMR spectra of the corresponding Mosher esters. The absolute stereochemistry of alcohol 4a was determined by hydrolysis of its oximino nitrile group followed by conversion into its corresponding alpha-hydroxy ester. The beta-hydroxy-alpha-oximino nitrile products were further submitted to oxime-and nitrile-selective transformations. This chemo- and stereoselective reduction can be used to generate important chiral building blocks.
Authors
I am an author on this paper
Click your name to claim this paper and add it to your profile.
Reviews
Recommended
No Data Available