Racochote S.Naweephattana P.Surawatanawong P.Kuhakarn C.Leowanawat P.Reutrakul V.Soorukram D.Mahidol University2023-09-162023-09-162023-01-01Organic and Biomolecular Chemistry (2023)14770520https://repository.li.mahidol.ac.th/handle/20.500.14594/90037Base-catalyzed diastereodivergent thia-Michael addition of thiols to chiral β-trifluoromethyl-α,β-unsaturated N-acylated oxazolidin-2-ones is reported. By tuning the base-catalyst (i-Pr2NEt, DABCO, or P2-t-Bu), a range of chiral thia-Michael adducts was synthesized in good yields with high diastereoselectivities. A plausible mechanism was proposed on the basis of the experimental results. This work is complementary to the existing methods offering advantages, e.g., switchable diastereoselectivity using a readily synthesized chiral starting material, a cheap and readily available base catalyst, and a simple and practical operation, enabling synthetic application in organic synthesis.ChemistryArticleSCOPUS10.1039/d3ob00999h2-s2.0-85170264415