Enamine Synthesis via Regiocontrolled 6-endo-dig and 5-exo-dig Tethered Carboamination of Propargylic Alcohols.

Autor:	Solé-Àvila H; Laboratory of Catalysis and Organic Synthesis and NCCR Catalysis, Institut des Sciences et Ingénierie Chimique, École Polytechnique Fédérale de Lausanne, 1015, Lausanne, Switzerland., Puriņš M; Laboratory of Catalysis and Organic Synthesis and NCCR Catalysis, Institut des Sciences et Ingénierie Chimique, École Polytechnique Fédérale de Lausanne, 1015, Lausanne, Switzerland., Eichenberger L; Laboratory of Catalysis and Organic Synthesis and NCCR Catalysis, Institut des Sciences et Ingénierie Chimique, École Polytechnique Fédérale de Lausanne, 1015, Lausanne, Switzerland., Waser J; Laboratory of Catalysis and Organic Synthesis and NCCR Catalysis, Institut des Sciences et Ingénierie Chimique, École Polytechnique Fédérale de Lausanne, 1015, Lausanne, Switzerland.
Jazyk:	angličtina
Zdroj:	Angewandte Chemie (International ed. in English) [Angew Chem Int Ed Engl] 2024 Dec 09; Vol. 63 (50), pp. e202411383. Date of Electronic Publication: 2024 Oct 24.
DOI:	10.1002/anie.202411383
Abstrakt:	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. (© 2024 The Authors. Angewandte Chemie International Edition published by Wiley-VCH GmbH.)
Databáze:	MEDLINE
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