Catalytic Asymmetric Tandem Reaction of o-Alkynylbenzaldehydes, Amines, and Diazo Compounds

An efficient asymmetric tandem reaction of o-alkynylbenzaldehydes, amines, and diazo compounds catalyzed by chiral silver imidodiphosphate has been established. Chiral 1,2-dihydroisoquinoline analogues have a tertiary stereocenter at the C1 position, and substituents at the C3 position are available with up to 97% yields and 98% ee. These products can be elaborated into the corresponding beta-aminophosphonates or PARP1-inhibitor analogues.

Automated summary

An efficient asymmetric tandem reaction catalyzed by chiral silver imidodiphosphate has been developed for the synthesis of chiral 1,2-dihydroisoquinoline analogues with a tertiary stereocenter at the C1 position. The products can be further elaborated into beta-aminophosphonates or PARP1-inhibitor analogues with high yields and ee values.