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The first time steroselective synthesis of (Z)-β-bromo Baylis–Hillman ketones has been achieved using a one-pot three-component reaction. The new system uses MgBr 2 as both the Lewis acidic promoter and the bromine source for the Michael-type addition with α,β-acetylenic ketones to form an active β-bromo allenolate intermediate, which in turn attacks various aldehydes to afford β-bromo Baylis–Hillman...
A highly stereoselective method for the synthesis of (E)-β-halogeno Baylis-Hillman adducts has been developed. The new method involves a tandem α-hydroxyalkylation/β-chlorination of α,β-acetylenic ketones by using TiCl 4 as the chlorine source for α,β-conjugate addition, and concurrently as the Lewis acid promoter for the carbonyl addition. The new system tolerates a broad scope of reactants...
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