Abstract
Abstract Hetero Diels-Alder reactions of optically active 3-(p-tolylsulfinyl)-2-furaldehyde with 1-methoxy-3-(trimethylsilyloxy)-buta-1,3-diene (Danishefsky's diene) in the presence of a Lewis acid has been examined. The reaction in the presence of 1.0 equiv. of Ln(OTf)3 (Ln = Yb, Nd and Sm) followed by acidic work-up produced in good yields (68–88%) the hetero Diels-Alder adduct with high diastereoisomeric excesses (93–98% d.e.'s), whereas in the presence of an NMR shift reagent, tris(2,2,6,6-tetramethyl-3,5-heptanedionate)europium [Eu(thd)3] the corresponding diastereoisomer was obtained as the major adduct in excellent yield with 77% d.e.
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