Kinetic Resolution of α-Nitrolactones by Catalytic Asymmetric Hydrolysis or Ester–Amide Exchange Reaction

Abstract

C 1-Symmetric chiral ammonium salt catalysts induced a kinetic resolution of racemic α-nitrolactones through an asymmetric ester–amide exchange reaction. The corresponding amides were obtained with high enantioselectivities and high S (= k fast/k slow) values. This reaction system is a useful approach for obtaining carbocyclic quaternary α-nitroamides as chiral building blocks.

Synthesis and Characterization of Multiple Functionalized Cyclohexanone Using Diels–Alder Reaction of α-Nitrocinnamate

“…However, there have been few examples of the Diels-Alder reaction using α-carbonylated nitroalkenes [12][13][14][15][16][17][18][19] despite abundant studies on that using α-unsubstituted nitroalkenes [1, 3,4]. However, related studies of heterocyclic compounds such as coumarin [20,21], quinolone [22][23][24], pyridone [24] and pyridazine [25] possessing an α-carbonylated nitroalkene moiety as a partial structure have been reported. Accordingly, systematic studies using α-carbonylated nitroalkene can help expand the synthetic utility of the Diels-Alder reaction.…”