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An efficient method for the α-chlorination of ketones under basic conditions is described using methyl chlorosulfate. Its applicability for the chlorination of other functional groups has also been studied and it is equally useful for the synthesis of α-chloroesters and amides. Methyl chlorosulfate is described for the first time as a positive chlorine source. Some aldol reactions which occur during the chlorination of some substrates are also reported. [ABSTRACT FROM AUTHOR]

A series of novel ( E )-5,5-dimethyl-3-styrylcyclohex-2-en-1-ol dienes were synthesized by reduction of the respective ketones and their Diels–Alder reactivity explored with N -phenylmaleimide and methyl acrylate. Consequently, two groups of novel products were synthesized in high yields. In reactions with N -phenylmaleimide, the initially formed cycloadducts undergo an additional in situ lactonization to give tricyclic lactone systems, due to spontaneous attack of the allylic hydroxyl on the neighboring carbonyl group of the dienophile residue. All reactions proceeded stereoselectively to give solely the endo products. [ABSTRACT FROM AUTHOR]

Abstract: Exploratory studies towards the preparation of potential HIV-1 protease and integrase inhibitors have led to the synthesis of Baylis–Hillman-derived N,N′-disubstituted piperazines. X-ray crystallographic, computer modelling and NMR techniques have been used to elucidate questions concerning configurational preferences, reaction pathways and the apparent difference in susceptibility towards aza-Michael reactions exhibited by methyl acrylate and methyl vinyl ketone (MVK) derived Baylis–Hillman substrates. [Copyright &y& Elsevier]