Work

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

Year: 2024

Type: article

Abstract: 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.

Source: Angewandte Chemie International Edition

DOI: 10.1002/anie.202411383

Authors: Helena Solé‐Àvila, Mikus Puriņš, Lucas Eichenberger, Jerome Waser

Institutions: NCCR Catalysis, École Polytechnique Fédérale de Lausanne

Language: English

Topic: Catalytic Alkyne Reactions

Subfield: Organic Chemistry

Field: Chemistry

Domain: Physical Sciences

Open Access status: hybrid

Estimated APC paid: $5,510

Funders: École Polytechnique Fédérale de Lausanne, Schweizerischer Nationalfonds zur Förderung der Wissenschaftlichen Forschung, H2020 European Research Council, HORIZON EUROPE European Research Council