title: Switching the reactivity of dihydrothiopyran-4-one with aldehydes by aqueous organocatalysis: Baylis-Hillman, aldol, or aldol condensation reactions.
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.
authors: Department of Organic Chemistry, Chemistry & Chemical Engineering Research Center of Iran, P.O. Box 14335-186, Tehran, Iran. abaee@ccerci.ac.ir
authors: M Saeed
authors: MS
authors: Abaee
authors: Mohammad M
authors: MM
authors: Mojtahedi
authors: Ghasem F
authors: GF
authors: Pasha
authors: Elahe
authors: E
authors: Akbarzadeh
authors: Abbas
authors: A
authors: Shockravi
authors: A Wahid
authors: AW
authors: Mesbah
authors: Werner
authors: W
authors: Massa