Easy Access to 2,4-Disubstituted Cyclopentenones by a Gold(III)-Catalyzed A3-Coupling/Cyclization Cascade

Abstract

An efficient and convenient synthesis of 2,4-disubstituted cyclopentenones has been achieved through a Au(III)catalyzed isomerization−A3-coupling/cyclization cascade. A possible mechanism involving an initial Au(III)-catalyzed isomerization, A3type coupling, and cyclization via an enol intermediate is postulated.

Microwave-assisted decarboxylative reactions: advanced strategies for sustainable organic synthesis

“…Over the last decade, substantial progress has been achieved in the development of A 3 -coupling. 48–55 Due to the inherent advantage of C–C bond formation under relatively neutral conditions in the decarboxylative reactions, decarboxylative A 3 -coupling has been widely used as an alternative strategy for constructing propargylamines. 56–65…”

“…Over the last decade, substantial progress has been achieved in the development of A 3coupling. [48][49][50][51][52][53][54][55] Due to the inherent advantage of C-C bond formation under relatively neutral conditions in the decarboxylative reactions, decarboxylative A 3 -coupling has been widely used as an alternative strategy for constructing propargylamines. [56][57][58][59][60][61][62][63][64][65] In 2011, Van der Eycken and co-workers 66 described a copper-catalyzed three-component decarboxylative coupling of α-keto acids 27 with amines 28 and terminal alkynes 29 under microwave irradiation (Scheme 12a).…”

Upgrading furanic platforms to α-enaminones: tunable continuous flow hydrogenation of bio-based cyclopentenones

“…1b): (1) the conventional multistep synthesis from diketones; [11][12][13][14][15][16] (2) cyclic ketone oxidative coupling with anilines or O-benzoylhydroxylamines under mild conditions, including electrochemical methods; [17][18][19][20][21] more recently, (3) a threecomponent gold-catalysed coupling/cyclization reaction. 22 Fig. 1 a) Importance of the α-enaminone core in biological active compounds and precursors; b) reported methods for the synthesis of α-enaminones; and c) proposed work towards the preparation of α-enaminones from furfural applying a more sustainable continuous flow hydrogenation of DCPs.…”

Chemodivergent Synthesis of Oxazolidin-2-ones via Cu-Catalyzed Carboxyl Transfer Annulation of Propiolic Acids with Amines

“…In these reactions, different strategies to selectively generate structurally divergent propargylamines from the same set of amines and alkynes by tuning the reaction conditions were reported . Despite numerous reports centered on the generation of propargylamines, there is little insight into their reactivity for in situ application in synthetic transformations . Inspired by the above-mentioned chemodivergent coupling of amines with alkynes and intrigued by the underexplored carboxyl transfer of carboxylic acids, herein, we report the first selective carboxyl transfer annulation of propiolic acids with amines for the divergent access to polysubstituted oxazolidin-2-ones (Scheme c).…”