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We focused on neighboring group participation as a key step for controlling the structures of cationic intermediates, and developed a valuable cation precursor, 2, 2-dimethoxyethyl ester, as well as selective reactions directed by a sulfenyl group. It was found that 2, 2-dimethoxyethyl esters generate cyclic cationic intermediates on the action of a Lewis acid via neighboring group participation of the ester function toward the acetal carbon. The cationic intermediates thus generated were useful for the stereoselective Michael reaction as well as the Diels-Alder reaction. The reactions applying neighboring effect of a sulfenyl group were also examined. As a result, stereoselective aldol reactions of the substrates containing a sulfenyl group were developed. Moreover, regioselective pinacol rearrangement and allylation reaction, and stereoselective cationic cyclization could be effectively carried out under the control of a sulfenyl group.

Selective Synthetic Reactions Applying Neighboring Group Participation.