Copper-catalyzed multicomponent reaction of β -trifluoromethyl β -diazo esters enabling the synthesis of β -trifluoromethyl N,N-diacyl- β -amino esters

Abstract
An efficient multicomponent reaction of newly designed β-trifluoromethyl β-diazo esters, acetonitrile, and carboxylic acids via an interrupted esterification process under copper-catalyzed conditions has been developed, which affords various unsymmetrical β-trifluoromethyl N,N-diacyl-β-amino esters in good to excellent yields. The reaction features mild conditions, a wide scope of β-amino esters and carboxylic acids, and also applicability to large-scale synthesis, thus providing an efficient way for the synthesis of β-trifluoromethyl β-diacylamino esters. Furthermore, this reaction represents the first example of a Mumm rearrangement of β-trifluoromethyl β-diazo esters.

Beilstein J. Org. Chem. 2024, 20, 212–219. doi:10.3762/bjoc.20.21

Source: Beilstein Journal of Organic Chemistry - February 2, 2024 Category: Chemistry Authors: Beilstein Journal of Organic Chemistry - Syndicated Feeds Tags: β -carbonyl diazo copper catalyst fluoroalkyl diazo Mumm rearrangement unsymmetrical -diacylamino esters Letter Source Type: research