Journal of Organic Chemistry p. 1802 - 1804 (1989)
Update date:2022-07-30
Topics:
Ohta, Hiromichi
Kobayashi, Naoki
Ozaki, Kazuhiko
Reduction of a number of 1-nitro-1-alkenes by fermenting bakers' yeast has been found to be enantioselective, resulting in the formation of optically active 1-nitroalkanes.In most cases, optical purities of the products determined by HPLC analysis of MTPA amides were as high as 83-98percent ee.The optimum rate of conversion was obtained when the reaction was carried out at pH 8 and low concentration of substrates.The absolute configuration of resulting (+)-1-nitro-2-phenylpropane was determined to be R by comparing the specific rotation with that of an authentic specimen after reductive hydrolysis to the corresponding aldehyde.
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