Department of Chemistry , Duke University , Durham , North Carolina 27708 , United States.
Org Lett. 2020 Feb 21;22(4):1681-1685. doi: 10.1021/acs.orglett.0c00342. Epub 2020 Feb 4.
We describe a strategy for the enantio- and diastereoselective synthesis of homoallylic α-trifluoromethyl amines by the catalytic hydroalkylation of terminal dienes. Trifluoromethyl-substituted isatin-derived azadienolate nucleophiles undergo γ-selective alkylation with a Pd-DTBM-SEGPHOS catalyst, which additionally promotes regioselective addition to the diene and delivers products in up to 86% yield, 10:1 dr, and 97.5:2.5 er.
我们描述了一种通过末端二烯的催化氢烷基化反应来对同烯丙基 α-三氟甲基胺进行对映选择性和非对映选择性合成的策略。三氟甲基取代的色氨酸衍生的氮杂二烯醇化物亲核试剂与 Pd-DTBM-SEGPHOS 催化剂进行γ选择性烷基化,该催化剂还促进了与二烯的区域选择性加成,并以高达 86%的收率、10:1 的 dr 和 97.5:2.5 的 er 提供产物。