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.

中文翻译：

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邻苯二醌单缩醛的合成与反应

描述了邻-苯醌单半缩醛的制备和反应。带有氨基醇基团的酚的氧化脱芳香化作用引起N-环化作用，从而得到邻苯二醌单半缩醛。当手性氨基醇用作取代基时，N-环化立体选择性地提供产物。如所预期的，手性邻苯并醌单缩醛经过立体选择性Diels-Alder反应与缺电子的烯烃反应，证实了邻苯并醌单缩醛的应用前景广阔。