Diastereoselective Michael Addition of Non‐Functionalized Furanone to Nitroalkenes in Aqueous Condition

Abstract

Selectivity plays a major role in organic chemistry and biological applications. Herein, we present a diastereoselective DMAP‐catalyzed Michael addition of furanone (butenolide) to nitroalkenes. Notably, our method does not require the pre‐activation of furanone as 2‐(trimethylsiloxy)furan and utilizes water: ethanol (1:3) as a solvent. These mild conditions afford the anti‐Michael products in up to 82% isolated yield with up to 87:13 dr (diastereomeric ratio). The scope of this reaction extends to various aromatic, heteroaromatic, and aliphatic nitroalkenes. Furthermore, we demonstrate this process on a gram scale and highlight the utility of the obtained Michael adducts for accessing natural product cores.