Enantio- and Diastereoselective Synthesis of Homoallylic α-Trifluoromethyl Amines by Catalytic Hydroalkylation of Dienes
Enantio- and Diastereoselective Synthesis of Homoallylic α-Trifluoromethyl Amines by Catalytic Hydroalkylation of Dienes
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DOI：
10.1021/acs.orglett.0c00342
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发表时间：
2020-02-21
期刊：
影响因子：
5.2
通讯作者：
Malcolmson, Steven
中科院分区：
文献类型：
--
作者：
Onyeagusi, Chibueze, I;Shao, Xinxin;Malcolmson, Steven
我们描述了一种通过催化末端二烯的氢烷基化，对映和非对映选择性合成同丙烯基α -三氟甲基胺的策略。在Pd-DTBM-SEGPHOS催化剂的作用下，三氟甲基取代的异嘌呤衍生的氮二烯酸酯亲核试剂进行γ选择性烷基化反应，进一步促进了二烯的区域选择性加成，并以高达86%的收率、10:1 dr和97.5:2.5 er的速率生成产物。
We describe a strategy for the enantio- and diastereoselective synthesis of homoallylic alpha-trifluoromethyl amines by the catalytic hydroalkylation of terminal dienes. Trifluoromethyl-substituted isatin-derived azadienolate nucleophiles undergo gamma-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.