[4+2] cycloadditions of nitroalkenes in water. Highly asymmetric synthesis of functionalized nitronates

The [4 + 2] cycloadditions of (E)-2-aryl-1-cyano-1-nitroalkenes 1 with achiral and enantiopure vinyl ethers 2 and 3 carried out in sole water are reported. These reactions occur in a heterogeneous phase under mild conditions and are fast and highly stereoselective. By using(-)-N,N-dicyclohexyl-(1S)-isoborneol-10-sulfonamide as achiral auxiliary, the cycloadditions are totally asymmetric. The face selectivity is discussed in terms of the shape of the chiral auxiliary and the reactive conformation of vinyl ether.