Atroposelective organocatalytic synthesis of 1,2′-binaphthalene-3′-carbaldehydes under mechanochemical conditions

Abstract

Ball-milling allowed the efficient realization of asymmetric organocatalytic Michael/aldol cascade, which affords 1′,2′-dihydro-1,2′-binaphthalene derivatives. These compounds were transformed into axially chiral 1,2′-binaphthalene-3′-carbaldehydes under mechanochemical conditions. Evaluation of milling parameters such as frequency or liquid-assisting agents led to optimum reaction conditions, which afforded products in high yields, and short times while preserving high enantiomeric purity.