Two-Step Synthesis of α,β-Unsaturated γ-Amino Acid Esters via N-Heterocyclic Carbene Catalyzed [4+2] Cycloaddition of Enals and Nitroso Compounds

An efficient strategy for the synthesis of various of α,β-unsaturated γ-amino acid esters has been established employing N-heterocyclic carbene catalyzed [4+2] cycloadditions of β-methyl enals and aromatic nitroso compounds to afford 1,2-oxazin-6-ones in good yields. A subsequent acid-catalyzed esterification under ring opening yields the γ-amino enoates in good yields.

Brønsted acid mediated N–O bond cleavage for α-amination of ketones through the aromatic nitroso aldol reaction

A Brønsted acid mediated N–O bond cleavage for α-amination of ketones has been developed through the nitroso aldol reaction of less-reactive aromatic nitroso compounds and silyl enol ethers having a disilane (–SiMe2TMS) backbone.

Crystal disordering and organic solid-state reactions

This investigation is a case study about the nature of the adiabatic organic solid-state reactions by kinetic measurements of the processes that occur during the dimerization of aromatic nitroso compounds under three different topochemical environments in crystals.