Enantioselective Oxidative Cyclization/Mannich Addition Enabled by Gold(I)/Chiral Phosphoric Acid Cooperative Catalysis
作者:Hanlin Wei、Ming Bao、Kuiyong Dong、Lihua Qiu、Bing Wu、Wenhao Hu、Xinfang Xu
DOI:10.1002/anie.201812140
日期:2018.12.21
An enantioselective Mannich‐type reaction of 3‐butynol and nitrones is described, which affords dihydrofuran‐3‐ones in good yields and with excellent enantioselectivities. The reaction is initiated by gold‐catalyzed alkyne oxidation and modification of the resulting gold carbene species with a tethered hydroxy group to form enolate species; the reaction terminates with an enantioselective Mannich‐type
描述了3-丁炔醇和硝酮的对映选择性曼尼希型反应,该反应可提供高收率和出色的对映选择性的二氢呋喃-3-酮。该反应是通过金催化的炔烃氧化反应以及将生成的带有链羟基的金卡宾物质改性而形成烯醇化物而引发的。反应在手性磷酸(CPA)和氢键的辅助下以对映选择性Mannich型加成终止。这种涉及化学键裂解,片段修饰和重组过程的新型炔烃转化模式,提供了一种原子经济和分步经济的方法,并且是通过α-氧代金在金催化的炔烃氧化中进行合作性不对称催化的第一个实例。卡宾路线。