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  • Title: Switching the reactivity of dihydrothiopyran-4-one with aldehydes by aqueous organocatalysis: Baylis-Hillman, aldol, or aldol condensation reactions.
    Author: Abaee MS, Mojtahedi MM, Pasha GF, Akbarzadeh E, Shockravi A, Mesbah AW, Massa W.
    Journal: Org Lett; 2011 Oct 07; 13(19):5282-5. PubMed ID: 21899295.
    Abstract:
    An aqueous medium containing catalytic amounts of a tertiary amine was employed to direct the chemoselectivity of the reaction of aldehydes with 1a. With DBU, 2 was formed at room temperature as a rare exemplary of Baylis-Hillman reactions in heterocyclic enones. DABCO alternated the pathway toward an aldol reaction to form syn/anti mixtures of 3 with the syn isomers being the major products. With Et(3)N, aldol condensation dominated.
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