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

Identifier:  imarina:9231944

Handle: https://hdl.handle.net/20.500.11797/imarina9231944

Authors:  Sendra, J; Reyes, E; Prieto, L; Fernández, E; Vicario, JL

Abstract:
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 α-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.