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Synthesis and Reaction of ortho-Benzoquinone Monohemiaminals. 2018
Department of Chemistry and Biochemistry, School of Advanced Science and Engineering, Waseda University , 3-4-1 Ohkubo, Shinjuku-ku, Tokyo 169-8555, Japan.
The preparation and reactions of ortho-benzoquinone monohemiaminals are described. The oxidative dearomatization of phenols bearing amino alcohol groups induced N-cyclization to afford ortho-benzoquinone monohemiaminals. The N-cyclization stereoselectively affords the product when a chiral amino alcohol is used as the substituent. The chiral ortho-benzoquinone monohemiaminal undergoes stereoselective Diels-Alder reactions with electron-deficient alkenes, as expected, confirming the promising utility of ortho-benzoquinone monohemiaminals.
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