Phosphazene-Catalyzed Cascade Esterification/Stereoselective Aza-Michael Addition of Chiral β-Trifluoromethyl-α,β-unsaturated N -Acylated Oxazolidin-2-ones

Racochote S.Kuhakarn C.Leowanawat P.Reutrakul V.Soorukram D.Mahidol University2025-03-132025-03-132024-08-05Synlett Vol.36 No.4 (2024) , 329-33409365214https://repository.li.mahidol.ac.th/handle/20.500.14594/106680Upon treatment of chiral β-trifluoromethyl-α,β-unsaturated N -acylated oxazolidin-2-ones with a range of alcohols using phosphazene base as a catalyst, the unexpected cascade esterification/stereoselective aza-Michael addition was observed. The reactions proceeded with high diastereoselectivities (up to >99:1) to give a series of enantioenriched aza-Michael addition products in good to high yields. The structure and stereochemistry of the representative aza-Michael adduct were confirmed by X-ray crystal structure analysis. The plausible mechanism was proposed on the basis of the experimental results.The synthetic transformations of chiral aza-Michael addition products were also demonstrated highlighting the synthetic application of the present work. 2024. Thieme. All rights reserved.ChemistryPhosphazene-Catalyzed Cascade Esterification/Stereoselective Aza-Michael Addition of Chiral β-Trifluoromethyl-α,β-unsaturated N -Acylated Oxazolidin-2-onesArticleSCOPUS10.1055/a-2364-61192-s2.0-8521812350414372096