通过催化二烯的氢烷基化反应对映选择性和非对映选择性合成偕丙基 α-三氟甲基胺。
Enantio- and Diastereoselective Synthesis of Homoallylic α-Trifluoromethyl Amines by Catalytic Hydroalkylation of Dienes.
机构信息
Department of Chemistry , Duke University , Durham , North Carolina 27708 , United States.
出版信息
Org Lett. 2020 Feb 21;22(4):1681-1685. doi: 10.1021/acs.orglett.0c00342. Epub 2020 Feb 4.
Abstract
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.
摘要
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。
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