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41.1.1.5.45 Method 45: Reduction of Nitroalkenes Using Biological and Biomimetic Reducing Agents

DOI: 10.1055/sos-SD-041-00002

Aitken, R. A.; Aitken, K. M.Science of Synthesis, (201041169.

The reduction of nitroalkenes to give the corresponding nitroalkanes has been achieved using a number of microorganisms, most notably bakers yeast, and in most cases the reduction is highly stereoselective (Scheme 238).[‌611‌,‌612‌] Detailed studies of substrate specificity showed that, while excellent enantiomeric excess and moderate diastereomeric excess are achieved for trisubstituted nitroalkenes, E-1,2-disubstituted nitroalkenes give only moderate enantiomeric excesses.[‌613‌] While the first studies were carried out in an aqueous medium, the use of petroleum ether has more recently allowed mechanistic studies[‌614‌] and the isolation of two specific nitroalkene reductases.[‌615‌] The use of Clostridium sporogenes to catalyze highly enantioselective nitroalkene reduction by hydrogen gas has also been reported.[‌616‌]

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