The reduction of (Z)-β-acylaminonitroalkenes catalyzed by ene-reductases is described for the first time. The reaction occurs with a high conversion and excellent enantioselectivity and shows a wide substrate scope. The reduced products are valuable chiral synthons characterized by two vicinal nitrogen-containing functional groups that can be further modified by functional group inter-conversion thanks to the synthetic versatility of the nitro moiety. The chemo-enzymatic synthesis of (R)-N,N′-(1-phenylethane-1,2-diyl)diacetamide from easily accessible (Z)-N-(2-nitro-1-phenylvinyl)acetamide is herein reported as a representative application of this synthetic procedure.

Asymmetric Bioreduction of beta-Acylaminonitroalkenes: Easy Access to Chiral Building Blocks with Two Vicinal Nitrogen-Containing Functional Groups

Elisabetta Brenna;Michele Crotti;Francesco G. Gatti;Fabio Parmeggiani;Sara Santangelo
2017-01-01

Abstract

The reduction of (Z)-β-acylaminonitroalkenes catalyzed by ene-reductases is described for the first time. The reaction occurs with a high conversion and excellent enantioselectivity and shows a wide substrate scope. The reduced products are valuable chiral synthons characterized by two vicinal nitrogen-containing functional groups that can be further modified by functional group inter-conversion thanks to the synthetic versatility of the nitro moiety. The chemo-enzymatic synthesis of (R)-N,N′-(1-phenylethane-1,2-diyl)diacetamide from easily accessible (Z)-N-(2-nitro-1-phenylvinyl)acetamide is herein reported as a representative application of this synthetic procedure.
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Utilizza questo identificativo per citare o creare un link a questo documento: https://hdl.handle.net/11311/1044788
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