Key Laboratory of Green Chemistry & Technology, Ministry of Education, College of Chemistry, Sichuan University, Chengdu 610064, China.
Org Lett. 2021 Nov 5;23(21):8419-8423. doi: 10.1021/acs.orglett.1c03101. Epub 2021 Oct 22.
A highly diastereo- and enantioselective allylation of isatins with 3-substituted allylboronic compounds was achieved by the chiral -dioxide/Lu(OTf) complex. This approach provides an efficient route to useful enantioenriched 3-allyl-3-hydroxyoxindoles with adjacent tetrasubstituted tertiary or tetrasubstituted quaternary stereogenic centers. Density functional theory calculations were performed to understand the different diastereoselection between the background reaction and catalytic process. Moreover, allylation with potassium allyltrifluoroborate was accomplished by the chiral -dioxide/In(OTf) complex. The synthetic utility was demonstrated by further transformation of the product to a tetrahydrofuranyl oxindole derivative.
手性双恶唑啉/Lu(OTf) 配合物实现了吲哚满酮与 3-取代烯丙基硼酸化合物的高非对映选择性和对映选择性烯丙基化反应。这种方法为具有相邻四取代三级或四取代季碳立体中心的有用的对映体富集 3-烯丙基-3-羟基吲哚满酮提供了一种有效的途径。进行了密度泛函理论计算，以理解背景反应和催化过程之间不同的非对映选择性。此外，手性双恶唑啉/In(OTf) 配合物还实现了与钾烯丙基三氟硼酸盐的烯丙基化反应。通过进一步转化产物为四氢呋喃基氧化吲哚衍生物，展示了该合成方法的实用性。
