Diastereodivergent Synthesis of 2‑Ene-1,4-hydroxy Sulfides from 2‑Sulfinyl Dienes via Tandem Sulfa-Michael/Sulfoxide-Sulfenate Rearrangement

The highly diastereoselective sulfa-Michael addition of thiolates to enantiopure 2-sulfinyl dienes leads to anti or syn 2- ene-1,4-hydroxy sulfides in good yields and selectivities dependent on the reaction conditions in a diastereodivergent process. Synthetic applications of these enantiopure hydroxy sulfides by subsequent sigmatropic rearrangements have been outlined.This research was supported by PID2019-107380GB-100 and CTQ2016-77555-C2-2-R.Peer reviewe