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Highly Stereoselective α-Hydroxyalkylation/Chlorination of α,β-Acetylenic Ketones—An Efficient Approach to β-Halogeno Baylis–Hillman Adducts

✍ Scribed by Han-Xun Wei; Sun Hee Kim; Thomas D Caputo; David W Purkiss; Guigen Li

Publisher
Elsevier Science
Year
2000
Tongue
French
Weight
327 KB
Volume
56
Category
Article
ISSN
0040-4020

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✦ Synopsis

A highly stereoselective method for the synthesis of (E)-b-halogeno Baylis-Hillman adducts has been developed. The new method involves a tandem a-hydroxyalkylation/b-chlorination of a,b-acetylenic ketones by using TiCl 4 as the chlorine source for a,bconjugate addition, and concurrently as the Lewis acid promoter for the carbonyl addition. The new system tolerates a broad scope of reactants in which aliphatic and aromatic a-acetylenic ketones can be subjected to the conjugate addition. Both aliphatic and aromatic aldehydes can also be employed as electrophilic acceptors. Good yields (61-88%) and high E/Z stereoselectivity have been obtained for the nine examples which were examined, only in one case was E/Z selectivity of 17/1 observed and the two individual isomers are separable via flash column chromatography.

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