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

DOI: 10.1002/ange.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: $5,250

Funders: École Polytechnique Fédérale de Lausanne, H2020 European Research Council, HORIZON EUROPE European Research Council