Organocatalytic Synthesis of Furan-Embedded Styrene Atropisomers

Herein, we report the first synthesis of furan-embedded styrene atropisomers via the reaction between 1-(aryl-ethynyl)-naphthalen-2-ol and ?-hydroxyenone. The reaction proceeds through in situ furan formation from ?-hydroxyenone. The styrene derivatives were obtained in moderate to good yields with high diastereoselectivities with a catalytic amount of PTSA. Few applications such as triazole formation and cross-coupling reactions have been demonstrated. A preliminary catalytic asymmetric version was also reported.

Automated summary

Here, we describe the first synthesis of furan-embedded styrene atropisomers by reacting 1-(aryl-ethynyl)-naphthalen-2-ol with α-hydroxyenone. The reaction involves in situ furan formation from α-hydroxyenone. With a catalytic amount of PTSA, the styrene derivatives are obtained in moderate to good yields with high diastereoselectivities. Various applications including triazole formation and cross-coupling reactions have been demonstrated, and a preliminary catalytic asymmetric version has also been reported.