Cai Ju, Wang Xin, Qian Yu, Qiu Lihua, Hu Wenhao, Xu Xinfang
School of Pharmaceutical Sciences , Sun Yat-sen University , Guangzhou 510006 , China.
Key Laboratory of Organic Synthesis of Jiangsu Province, College of Chemistry, Chemical Engineering and Materials Science , Soochow University , Suzhou 215123 , China.
Org Lett. 2019 Jan 18;21(2):369-372. doi: 10.1021/acs.orglett.8b03502. Epub 2018 Dec 31.
A novel gold-catalyzed oxidative cyclization/aldol addition of homopropargyl alcohols with isatins has been developed that provides an effective access to the 3-hydroxyoxindoles in high yields under mild reaction conditions with high diastereoselectivities. In comparison with disclosed transformations of alkyne oxidations via an α-oxo gold carbene route, this is the first example of an aldol-type interception of an ylide (or its enolate form) intermediate with alkyne as a safe and readily available nondiazo carbene precursor.
已开发出一种新型的金催化高炔丙醇与异吲哚酮的氧化环化/羟醛加成反应，该反应能在温和的反应条件下以高非对映选择性高产率有效地合成3-羟基氧化吲哚。与已公开的通过α-氧代金卡宾途径进行的炔烃氧化转化相比，这是首例以炔烃作为安全且易于获得的非重氮卡宾前体对叶立德（或其烯醇盐形式）中间体进行羟醛型截获的反应。
