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Asymmetric Bioreduction of β‐Acylaminonitroalkenes: Easy Access to Chiral Building Blocks with Two Vicinal Nitrogen‐Containing Functional Groups
Author(s) -
Brenna Elisabetta,
Crotti Michele,
Gatti Francesco G.,
Monti Daniela,
Parmeggiani Fabio,
Santangelo Sara
Publication year - 2017
Publication title -
chemcatchem
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.497
H-Index - 106
eISSN - 1867-3899
pISSN - 1867-3880
DOI - 10.1002/cctc.201700063
Subject(s) - vicinal , synthon , moiety , nitro , chemistry , acetamide , functional group , combinatorial chemistry , substrate (aquarium) , enantioselective synthesis , stereochemistry , catalysis , organic chemistry , alkyl , oceanography , geology , polymer
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.