Abstract
A practical enantioselective N-selective nitroso aldol reaction of α-methylmalonamates with a nitrosoarene is reported. The reaction employs the Takemoto thiourea catalyst for the induction of enantioselectivity, and the corresponding optically active oxyaminated malonamates were obtained in reasonably good yields.
Highlights
Nitrosoarenes are versatile building blocks frequently encountered in organic synthesis as precursors for the synthesis of nitrogen and oxygen-containing molecules [1-5]
There was a significant drop in the enantioselectivity when malonamates bearing substitutions at metaand ortho-positions were used, except for the reaction carried out using methoxy substitution at the 3-position where the corresponding oxyaminated product was obtained in 75% yield and
In addition to the methyl ester, the reaction was found to proceed smoothly with ethyl, tert-butyl, and p-methoxybenzyl esters of malonamate to furnish the oxyaminated products in good yields and moderate to good enantioselectivities (4o–u)
Summary
Nitrosoarenes are versatile building blocks frequently encountered in organic synthesis as precursors for the synthesis of nitrogen and oxygen-containing molecules [1-5]. Takemoto’s catalyst as the most efficient one for this transformation, our attempts to enhance the enantioselectivity centered on the variation of solvents. When the catalyst loading was reduced to 10 and 5 mol %, the enantioselectivity remained reasonably good, but the reaction yield was substantially affected.
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