Abstract Good-to-excellent diastereoselectivies have been achieved in the synthesis of 2H- chromans by Et 3 SiH/TMSOTf reductive deoxygenation of differently substituted 2- sulfinylmethylchroman-2-ols and their methyl ketals. The influence of both electron-donating and-withdrawing substituents on the sulfoxide and on the aromatic dihydobenzopyran core has been studied. SOR 1 electron-donating groups (R 1= pMeOPh and 2-MeO-1-naphthyl ...