Hokamp Tobias, Wirth Thomas
School of Chemistry, Cardiff University, Main Building, Park Place, Cardiff, CF10 3AT, UK.
Chemistry. 2020 Aug 17;26(46):10417-10421. doi: 10.1002/chem.202000927. Epub 2020 Jul 20.
An enantioselective catalytic synthesis of α-acetoxylated ketones through I(I)/I(III) catalysis using a resorcinol/lactamide-based chiral iodoarene is reported. Catalyst turnover by in situ generation of the active iodine(III) derivative is achieved by oxidation with mCPBA in the presence of acetic acid. The prior transformation of ketones to easily accessible acetyl enol ethers is beneficial and yields up to 97 % with enantioselectivities up to 88 % ee are obtained using only low catalyst loadings of only 5 mol % under mild reaction conditions.
报道了一种通过使用基于间苯二酚/内酰胺的手性碘芳烃，以I(I)/I(III)催化对α-乙酰氧基化酮进行对映选择性催化合成的方法。通过在乙酸存在下用间氯过氧苯甲酸氧化原位生成活性碘(III)衍生物来实现催化剂的周转。将酮预先转化为易于获得的乙酰烯醇醚是有益的，并且在温和的反应条件下仅使用5 mol%的低催化剂负载量，产率高达97%，对映选择性高达88% ee。
