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Bismuth(III)‐Triflate‐Catalyzed Highly Diastereoselective Synthesis of Substituted Tetrahydrothiophene via Tandem Isomerization, Michael and Aldol Reactions
Author(s) -
Borthakur Upasana,
Saikia Anil K
Publication year - 2019
Publication title -
chemistryselect
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.437
H-Index - 34
ISSN - 2365-6549
DOI - 10.1002/slct.201902871
Subject(s) - aldol reaction , tetrahydrothiophene , trifluoromethanesulfonate , chemistry , michael reaction , isomerization , catalysis , ketone , medicinal chemistry , diol , cascade reaction , organic chemistry
Bismuth(III)trifluoromethanesulfonate (Bi(OTf) 3 ) catalyzes the reaction of β,γ‐unsaturated ketone and 1,4‐dithiane‐2,5‐diol to afford highly substituted tetrahydrothiophenes via sequential rearrangement, Michael and aldol reactions in good yields. The reaction is highly diastereoselective. Bi(OTf) 3 acts as a catalyst for all three reactions.