Chiral Lewis Acid Promoted Asymmetric Michael Addition Reaction of 2-(Trimethylsilyloxy)furans

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Abstract
Lewis acid promoted Michael addition of 2-(trimethylsilyloxy)furan to 3-[(E)-2-butenoyl]-1,3-oxazolidin-2-one (2) was examined. A 1:1 complex prepared from scandium triflate and 3,3'-bis(diethylaminomethyl)-1,1'-bi-2-naphthol 5b in situ showed excellent anti-selectivity and moderate enantioselectivity, while Cu(II)-bis(oxazolines) complex exhibited excellent enantioselectivity and moderate to good anti-selectivity.

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