Intramolecular tandem seleno-Michael/aldol reaction followed by an oxidation-elimination process can be an efficient tool for the construction of hydroxy cyclo-1-ene-1-carboxylate esters from oxo-α,β-unsaturated esters. Generation of lithium selenolate from elemental selenium and n-BuLi provides a simple and efficient one-pot access to cyclic endo-Morita-Baylis-Hillman adducts.

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A new approach to gram scale synthesis of carbasugar derivatives via intramolecular seleno-Michael/aldol reaction.

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Carbasugars are a wide group of carbohydrate mimetics in which the ring oxygen had been replaced by a methylene group. The high importance of these compounds is related to their interesting biological and pharmacological properties which are the matter of current studies. In our work, concise synthesis of carbasugars from naturally occurring D-pentoses is presented. The onepot seleno-Michael reaction connected with intramolecular aldol reaction is a key step of the carbasugar core asymmetric synthesis. Further transformation of obtained carbasugar moiety led to different bioactive compounds. Tandem seleno-Michael reaction conjugated with oxidation/elimination step of in situ generated nucleophile has been described a few years ago in the intermolecular variant. In our work, we present the first example of this reaction in an intramolecular way which leads to a previously inaccessible cyclic product of Morita-Baylis-Hillman reaction. Conducted experiments allowed to receive cyclic products with high yields and good diastereoisomeric excesses.