Abstract
A highly diastereoselective C-2 alkylation of sugar derived cyclic enone 1 in the presence of diethylaluminium iodide by utilizing Morita–Baylis–Hillman chemistry is reported. While diethylaluminium iodide was found to be a suitable Lewis acid for this transformation, the widely employed TiCl4 was ineffective. A plausible mechanism, which considered the involvement of a Zimmerman–Traxler type of closed transition state and an orthoester intermediate, has been discussed.
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