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3位含有季碳手性中心的吲哚啉并环化合物是一类非常重要的化合物,广泛存在于各种天然产物和具有生物活性的分子中.化学家们发展了多种有效的途径来合成这类化合物.其中以方便易得的吲哚衍生物为起始原料,利用不对称去芳构化环化串联的方法最为简单高效,但多数工作都是从色胺或色醇衍生物出发,合成二氢吡咯并吲哚啉或二氢呋喃并吲哚啉化合物.因此,发展其他类型的吲哚衍生物的不对称去芳构化环化反应显得非常有必要.作者课题组发展了手性磷酸催化的吲哚衍生物与甲基乙烯基酮的不对称Michael加成环化串联反应.以5 mol%(R)-SPINOL为骨架的手性磷酸(R)-4c为催化剂,以中等到良好的收率和优秀的对映选择性构建了一系列手性吲哚[2,3-b]并氢化喹啉化合物,而且该催化体系对于克级规模反应同样能够获得很好的结果.
The 3 indolinyl ring compounds containing quaternary chiral centers are a very important class of compounds that are found in a wide variety of natural and bioactive molecules. Chemists have developed a variety of effective routes to synthesize Among these compounds, indole derivatives with easy availability are the simplest and most efficient methods to asymmetrically dearomatize ’’ ’’ s cyclization, but most of the work is from tryptamine or alcohol derivatives Starting from the synthesis of dihydropyrroloindoline or dihydrofuroindoline compounds. Therefore, the development of other types of indole derivatives asymmetric dearomatization cyclization reaction is very necessary. The asymmetric Michael addition of cyclohexylphosphonic acid catalyzed indole derivatives to methyl vinyl ketone was also developed. The chiral phosphate (R) -4c with 5 mol% (R) -SPINOL as the backbone As a catalyst, a series of chiral indole [2,3-b] and hydroquinoline compounds were constructed with moderate to good yields and excellent enantioselectivity, and the catalytic system was also available for gram-scale reactions Very good result.