Solé-Àvila Helena, Puriņš Mikus, Eichenberger Lucas, Waser Jerome
Laboratory of Catalysis and Organic Synthesis and NCCR Catalysis, Institut des Sciences et Ingénierie Chimique, École Polytechnique Fédérale de Lausanne, 1015, Lausanne, Switzerland.
Angew Chem Int Ed Engl. 2024 Dec 9;63(50):e202411383. doi: 10.1002/anie.202411383. Epub 2024 Oct 24.
Enamines are versatile building blocks for the synthesis of biologically active compounds. Nevertheless, only a limited number of strategies have been reported for preparing trisubstituted enamines in a regio- and stereoselective manner. Herein, we report a regiocontrolled 6-endo and 5-exo tethered carboamination of propargylic alcohols for the synthesis of trisubstituted enamines. High regioselectivity was achieved through fine-tuning of the amine protecting group during the Pd-catalyzed carboamination. The introduced trifluoromethylated tether enables further stereoselective functionalizations, such as hydrogenation and fluorination.
烯胺是用于合成生物活性化合物的多功能结构单元。然而，以区域和立体选择性方式制备三取代烯胺的策略报道有限。在此，我们报道了一种区域可控的炔丙醇6-内型和5-外型 tethered 碳胺化反应，用于合成三取代烯胺。在钯催化的碳胺化反应过程中，通过对胺保护基团的微调实现了高区域选择性。引入的三氟甲基化 tether 能够实现进一步的立体选择性官能团化反应，如氢化和氟化反应。
