14367-98-7Relevant articles and documents
Organocatalytic asymmetric Michael/hemiacetalization/acyl transfer reaction of α-nitroketones with o-hydroxycinnamaldehydes: Synthesis of 2,4-disubstituted chromans
Maity, Rajendra,Pan, Subhas Chandra
, p. 1598 - 1608 (2018/03/08)
An organocatalytic asymmetric cascade Michael/hemiketalization/acyl transfer reaction between o-hydroxycinnamaldehydes and α-nitroketones is developed. Prolinol TMS ether catalyst in combination with benzoic acid was found to be the most effective for this reaction which proceeds through an equilibrium of lactols to provide a single diastereomer of enantiopure 2,4-disubstituted chromans.
Asymmetric Bioreduction of β-Acylaminonitroalkenes: Easy Access to Chiral Building Blocks with Two Vicinal Nitrogen-Containing Functional Groups
Brenna, Elisabetta,Crotti, Michele,Gatti, Francesco G.,Monti, Daniela,Parmeggiani, Fabio,Santangelo, Sara
, p. 2480 - 2487 (2017/07/12)
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.
Unexpected C-C bond cleavage of α-nitroketone in the presence of TsNBr2: A new pathway for C-N bond formation
Sarma, Manas Jyoti,Phukan, Prodeep
supporting information, p. 257 - 262 (2016/03/09)
A new catalyst-free protocol for C-N bond formation via the cleavage of α-nitroketone has been developed. When α-nitroketones are treated with TsNBr2 in the presence of potassium carbonate, unexpected cleavage of C(O)-CHNO2 bond of α-nitroketone was observed followed by the formation of corresponding amide. Various nitroketones could be converted to corresponding amide using this procedure.