Asymmetric synthesis of enantiopure α-sulfenyl dithioacetals and α-sulfenyl aldehydes

Abstract The BF3·Et2O promoted thiolytic cleavage of the diastereomeric oxazolidines (1′R)-2 and (1′S)-2 has been studied. The thioacetalisations took place with concomitant thioetherification at the carbinol centres, giving rise to the α-sulfenyl dithioacetals (α-SDTAs) (S)-3 and (R)-3 respectively. Selective manipulation of the latter compounds was also achieved. Thus, oxidative hydrolysis gave the corresponding α-sulfenyl aldehydes which were shown to be enantiopure.