351464-38-5Relevant academic research and scientific papers
[4 + 2] Cycloadditions of nitroalkenes in water. Highly asymmetric synthesis of functionalized nitronates
Fringuelli,Matteucci,Piermatti,Pizzo,Burla
, p. 4661 - 4666 (2001)
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 a chiral 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.
