Michael Reaction of Nitroalkanes with β‐Nitroacrylates under a Solid Promoter: Advanced Regio‐ and Diastereoselective Synthesis of Nitro‐Functionalized α,β‐Unsaturated Esters and 1,3‐Butadiene‐2‐carboxylates

Abstract

A new class of nitro-functionalized a,b-unsaturated esters has been prepared by a regio-and diastereoselective Michael addition of nitroalkanes to b-nitroacrylates, performed at room temperature, under carbonate on polymer as promoter, and in the presence of ethyl acetate as eco-friendly solvent. Moreover, by the modular choice of the reaction conditions the method allows the synthesis of 1,3-butadiene-2-carboxylates.

β‐Nitroacrylates: A Versatile and Growing Class of Functionalized Nitroalkenes

“…Recently, Ballini and co‐workers disclosed a new base‐promoted conjugate addition of nitroalkanes 85 to β‐nitroacrylates 1 for synthesizing a new class of nitro‐functionalized α,β‐unsaturated esters (Scheme ) …”