Chemo- and Stereoselective Reduction of β-Keto-α-oximino Nitriles by Using Baker's Yeast

Title
Chemo- and Stereoselective Reduction of β-Keto-α-oximino Nitriles by Using Baker's Yeast
Authors
모길웅강순방김유승이용섭이재욱금교창
Keywords
synthetic methods; biotransformations; reduction; chemoselectivity; enantioselectivity
Issue Date
2015-02
Publisher
European journal of organic chemistry
Citation
VOL 2015, NO 5, 1137-1143
Abstract
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.
URI
http://pubs.kist.re.kr/handle/201004/49407
ISSN
1434193X
Appears in Collections:
KIST Publication > Article
Files in This Item:
There are no files associated with this item.
Export
RIS (EndNote)
XLS (Excel)
XML


qrcode

Items in DSpace are protected by copyright, with all rights reserved, unless otherwise indicated.

BROWSE