Base-catalyzed diastereodivergent thia-Michael addition to chiral β-trifluoromethyl-α,β-unsaturated N-acylated oxazolidin-2-ones

Base-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 diastereo...

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Bibliographic Details
Main Author: Racochote S.
Other Authors: Mahidol University
Format: Article
Published: 2023
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Online Access:https://repository.li.mahidol.ac.th/handle/123456789/90037
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Institution: Mahidol University
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Summary:Base-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.