School of Chemistry, University of Hyderabad, C. R. Rao Road, Gachibowli, Hyderabad 500 046, India.
J Org Chem. 2022 Sep 16;87(18):12370-12385. doi: 10.1021/acs.joc.2c01652. Epub 2022 Aug 31.
An efficient method for the construction of sugar-derived chiral oxepanone-indole molecular hybrids is investigated. The reaction condition is optimized by monitoring the progress at various temperatures, with various solvents, and with different Lewis acid catalysts. Under optimized conditions, high stereoselectivity and efficiency are achieved in most of the formed cycloadducts. The accessibility of the strategy is evaluated by utilizing an array of carbohydrate-derived donor-acceptor cyclopropanes and variably substituted indole substrates. Additionally, quick access to the bridged indole-oxepanone framework is described by utilizing a diastereoselective (3+2) cycloaddition of aryl-substituted donor-acceptor cyclopropanes incorporated in a pyran ring.
研究了一种高效的糖衍生手性氧杂环戊酮-吲哚分子杂合体的构建方法。通过监测不同温度、不同溶剂和不同路易斯酸催化剂下的反应进展，优化了反应条件。在优化条件下，大多数形成的环加成物都具有高的立体选择性和效率。通过利用一系列糖衍生的给体-受体环丙烷和各种取代的吲哚底物，评估了该策略的可及性。此外，通过利用在吡喃环中并入的取代芳基的给体-受体环丙烷的非对映选择性（3+2）环加成，描述了桥接吲哚-氧杂环戊酮骨架的快速获得。
