Transannular Enantioselective (3+2) Cycloaddition of Cycloalkenone Hydrazones under Bronsted Acid Catalysis

Hydrazones derived from cycloalkenones undergo an enantioselective transannular formal (3 + 2) cycloaddition catalyzed by a chiral phosphoric acid. The reaction provides high yields and excellent stereocontrol in the formation of complex adducts with one or two alpha-tertiary amine moieties at the ring fusion, and these can be converted into very versatile stereodefined decalin- or octahydro-1H-indene-derived 1,3-diamines through simple reductive N-N cleavage.

Automated summary

Hydrazones derived from cycloalkenones undergo an enantioselective transannular formal (3 + 2) cycloaddition catalyzed by a chiral phosphoric acid, providing high yields and excellent stereocontrol in the formation of complex adducts. These adducts can be converted into versatile stereodefined decalin- or octahydro-1H-indene-derived 1,3-diamines through simple reductive N-N cleavage.