Chemodivergent and Diastereoselective Synthesis of γ-Lactones and γ-Lactams: A Heterogeneous Palladium-Catalyzed Oxidative Tandem Process

Abstract

A palladium-catalyzed oxidative tandem process of enallenols was accomplished within a homogeneous/heterogeneous catalysis manifold, setting the stage for the highly chemodivergent and diastereoselective synthesis of γ-lactones and γ-lactams under mild conditions.

Efficient 1,3‐Oxazolidin‐2‐one Synthesis through Heterogeneous PdII‐Catalyzed Intramolecular Hydroamination of Propargylic Carbamates

“…For example, this Pd II ‐AmP‐MCF catalyst has been employed for the cycloisomerization of alkynoic acids and for the oxidative carbocyclization–borylation of enallenols . Additionally, this Pd II ‐AmP‐MCF could be utilized as a catalyst in the chemodivergent syntheses of γ‐lactones and γ‐lactams by different oxidative tandem processes …”

“…[16] Additionally, this Pd II -AmP-MCF could be utilized as ac atalyst in the chemodivergents yntheses of g-lactones and g-lactams by different oxidative tandem processes. [17] Following up on this work,w ew ere interested in studyingif our Pd II -AmP-MCF catalyst could also be used for the related cycloisomerization of propargyl carbamates to the correspond-ing 1,3-oxazolidin-2-ones. Here, our goal was to develop a more practical and recyclable heterogeneous system for the preparation of these valuablec ompounds (Scheme 1).…”

Palladium-catalyzed oxidative dehydrogenative carbonylation reactions using carbon monoxide and mechanistic overviews

“…More recently, this group developed a palladium-catalyzed oxidative carbonylation reaction of enallenols for the chemodivergent synthesis of g-lactone and g-lactam derivatives (Scheme 31). 39 Interestingly, the catalyst-controlled chemodivergent carbonylation forming products 45 and 46, respectively, was achieved by switching between homogeneous and heterogeneous catalysts.…”

Alkyne–Alkene [2 + 2] cycloaddition based on visible light photocatalysis

“…Intense research efforts have been made to develop efficient synthesis. For example, a number of elegant synthesis 1,3-dienes based on transition metal-catalysis including gold [49][50][51] , palladium 52,53 , and platinum 54,55 . Also, enyne metathesis with Grubbs catalysts has proven to be an efficient method for the synthesis of various 1,3-dienes 56,57 .…”