Asymmetric Bioreduction of β‐Acylaminonitroalkenes: Easy Access to Chiral Building Blocks with Two Vicinal Nitrogen‐Containing Functional Groups. Issue 13 (29th May 2017)

• Record Type: Journal Article
• Authors: Brenna, Elisabetta; Crotti, Michele; Gatti, Francesco G.; Monti, Daniela; Parmeggiani, Fabio; Santangelo, Sara
• Is Part Of: ChemCatChem. Volume 9:Issue 13(2017)
• Page Start: 2480
• Page End: 2487
• Publication Date: 2017-05-29
• Subjects: biocatalysis -- biotransformations -- enantioselectivity -- enzymes -- reduction; Catalysis -- Periodicals; 541.39505
• DOI: 10.1002/cctc.201700063
• Languages: English
• ISSNs: 1867-3880

Abstract

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. Abstract : Two birds with one stone : The reduction of ( Z )‐β‐acylaminonitroalkenes catalyzed by ene‐reductases occurs with a high conversion and excellent enantioselectivity to give access to valuable chiral synthons that bear two vicinal nitrogen‐containing functional groups.