Asymmetric 1,3-dipolar cycloadditions to 5-menthyloxy-2[5H]-furanones.

Metal Complexes versus Organocatalysts in Asymmetric 1,3-Dipolar Cycloadditions

Iridium–catalyzed 1,3–dipolar cycloadditions

1,3–Dipolar cycloaddition reactions (DCR) are atom–economic processes that permit the construction of heterocycles. Their enantioselective versions allow for the creation of up to four adjacent chiral centers in a concerted fashion. In particular, well–defined half–sandwich iridium (III) catalysts have been applied to the DCR between enals or methacrylonitrile with nitrones. Excellent yield and...

Enantioselective copper-catalyzed 1,3-dipolar cycloadditions.

1,3-Dipolar cycloadditions: applications to the synthesis of antiviral agents.

In the present perspective the advances and real possibilities of 1,3-dipolar cycloadditions as key steps in the total synthesis of virus inhibitors are described. Azides, nitrones, and azomethine ylides are the most appropriate 1,3-dipoles for the synthesis of privileged structures with the highest biological responses against viruses.

Decreasing Distortion Energies without Strain: Diazo-Selective 1,3-Dipolar Cycloadditions.

The diazo group has attributes that complement those of the azido group for applications in chemical biology. Here, we use computational analyses to provide insights into the chemoselectivity of the diazo group in 1,3-dipolar cycloadditions. Dipole distortion energies are responsible for ∼80% of the overall energetic barrier for these reactions. Here, we show that diazo compounds, unlike azides...