Solvent-controlled diastereodivergent cascade synthesis of trisubstituted tetrahydrothiophenes utilizing polystyrene-supported amine

An efficient and solvent-controlled diastereodivergent thia-Michael/aldol cascade synthesis of tetrahydrothiophenes (THTs) has been developed. The cascade reaction is catalyzed by polystyrene-supported amine to afford trisubstituted tetrahydrothiophene derivatives in excellent yields and diastereoselectivities. A broad range of substrate tolerance is examined under two different solvents to access a library of diastereomeric THTs. Moreover, the polymer-supported amines can be recovered and reused for the cascade reaction. [GRAPHICS] .

Automated summary

An efficient and solvent-controlled diastereodivergent thia-Michael/aldol cascade synthesis of tetrahydrothiophenes (THTs) has been developed. The cascade reaction is catalyzed by polystyrene-supported amine to afford trisubstituted tetrahydrothiophene derivatives in excellent yields and diastereoselectivities. A broad range of substrate tolerance is examined under two different solvents to access a library of diastereomeric THTs. Moreover, the polymer-supported amines can be recovered and reused for the cascade reaction.