23496-31-3Relevant academic research and scientific papers
Asymmetric and Site-Selective [3 + 2]-Annulations for the Synthesis of High-Value Bicyclic Lactams
Kalaitzakis, Dimitris,Sofiadis, Manolis,Triantafyllakis, Myron,Daskalakis, Konstantinos,Vassilikogiannakis, Georgios
, p. 1146 - 1149 (2018)
Asymmetric and site-selective formal [3 + 2]-annulations of γ-alkyl-β,γ-unsaturated γ-lactams with α,β-unsaturated aldehydes have been developed. These organocatalysed transformations yield high value enantioenriched bicyclic γ-lactams with up to four new stereocenters (sometimes including a quarternary carbon). The overall transformation starts from simple and readily accessible furans and oversees a rapid, controlled, and dramatic enhancement in 3D complexity.
Transfer Hydrogenation of Levulinic Acid to γ-Valerolactone and Pyrrolidones Using a Homogeneous Nickel Catalyst
Jurado-Vázquez, Tamara,Arévalo, Alma,García, Juventino J.
, p. 445 - 450 (2021/01/18)
We report a well-defined homogeneous nickel-based catalyst using the complex [dippeNi(COD)] (dippe=1,2-bis(diisopropyl phosphino)ethane) as a catalytic precursor with high activity in the hydrogenation of levulinic acid (LVA) to yield γ-valerolactone (GVL) under relatively mild conditions (4 h, 120 °C); formic acid (FA) is the transfer hydrogenation agent in a dehydrogenation-hydrogenation process. Under optimized conditions, GVL was obtained with excellent yield (>99 %) and selectivity (>99 %). The Ni-catalyst was assessed in the LVA hydrogenation with a variety of primary amines using an excess of FA (4 eq) as hydrogen donor at 15 h and 170 °C to produce 2-pyrrolydones with excellent yield (>99 %) and fair to good selectivity (from 68 to 92 %).
The Power of Triplet and Singlet Oxygen in Synthesis: 2-Oxindoles, 3-Hydroxy-2-oxindoles, and Isatins from Furans
Triantafyllakis, Myron,Sfakianaki, Kalliopi,Kalaitzakis, Dimitris,Vassilikogiannakis, Georgios
supporting information, p. 3631 - 3634 (2018/06/26)
A straightforward synthesis of substituted 2-oxindoles, 3-hydroxy-2-oxindoles, and isatins has been developed. Easily accessible furans were transformed into tetrahydropyranopyrrolones by a singlet oxygen initiated cascade reaction sequence. An acid-catal
One-Pot Transformation of Simple Furans into Octahydroindole Scaffolds
Kalaitzakis, Dimitris,Triantafyllakis, Myron,Ioannou, Georgios I.,Vassilikogiannakis, Georgios
supporting information, p. 4020 - 4023 (2017/03/27)
A highly efficient and general singlet-oxygen-initiated one-pot transformation of readily accessible furans into octahydroindole scaffolds has been developed.
A convenient one-pot synthesis of polysubstituted pyrroles from N-protected succinimides
Kobeissi, Marwan,Yazbeck, Ogaritte,Chreim, Yamama
, p. 2523 - 2526 (2014/05/06)
The dienamine products formed by the reaction between polysubstituted succinimides and the Petasis reagent were subjected to isomerization under mild acidic conditions to give polysubstituted pyrroles in excellent yields (85-95%). The scope and limitations of this methodology are explored.
SUBSTITUTION OF 3H-FURAN-2-ONES IN AMINATION AND HYDROAMINATION REACTIONS
Morozova, N. A.,Sedavkina, V. A.,Egorova, A. Yu.
, p. 308 - 311 (2007/10/02)
The amination and hydroamination of 5-alkyl-3H-furan-2-ones and their 3-benzylidene- and 3-formyl-derivatives were studied.The characteristics of the reactions, the requirements for the nature of the nucleophilic reagents, and the reaction conditions leading to the destruction of the furan ring and recyclization to pyrrolidinone and pyrrolinone structures are indicated.
