Department of Chemistry, The Hong Kong University of Science and Technology, Clear Water Bay, Kowloon, Hong Kong SAR, China.
Angew Chem Int Ed Engl. 2017 Apr 10;56(16):4583-4587. doi: 10.1002/anie.201701947. Epub 2017 Mar 23.
Catalytic asymmetric N-alkylation of indoles and carbazoles represents a family of important but underdeveloped reactions. Herein, we describe a new organocatalytic strategy in which in situ generated aza-para-quinone methides are employed as the alkylating reagent. With the proper choice of a chiral phosphoric acid and an N-protective group, the intermolecular C-N bond formation with various indole and carbazole nucleophiles proceeded efficiently under mild conditions with excellent enantioselectivity and functional-group compatibility. Control experiments and kinetic studies provided important insight into the reaction mechanism.
吲哚和咔唑的不对称 N-烷基化反应是一类重要但尚未充分发展的反应。在此，我们描述了一种新的有机催化策略，其中原位生成的氮杂-对醌甲川化物被用作烷基化试剂。通过选择合适的手性磷酸和 N-保护基，在温和的条件下，各种吲哚和咔唑亲核试剂与氮杂-对醌甲川化物之间的分子间 C-N 键形成反应可以高效进行，并且具有优异的对映选择性和官能团兼容性。控制实验和动力学研究为反应机制提供了重要的见解。
