Multigram synthesis of an advanced nitroalkene intermediate: application in synthesis of octahydroindol-2-one derivative featuring diastereoselective Michael addition of diethylmalonate

Chain-Branched Polyhydroxylated Octahydro-1H-Indoles as Potential Leads against Lysosomal Storage Diseases

“…Michael addition of carbonyl synthetic equivalents to electron-deficient nitro alkenes has proven to be a promising method for the enantioselective synthesis of γ−nitro acids [27,28]. In this regard, carbasugar nitro olefins are suitable scaffolds for this and other synthetic purposes [29], although they are practically unexplored. They include in their structure a preformed carbocyclic ring bearing several hydroxy substituents in a well-defined spatial orientation and a nitroethylene subunit suitable for Michael addition of nucleophiles.…”

Synthesis and Recovery of Pyridine- and Piperidine-based Camphorsulfonamide Organocatalysts Used for Michael Addition Reaction

“…As important members of the camphor family, camphorsulfonamides were applied first as chiral auxiliaries [7][8][9][10], later as enantioselective organocatalysts [11][12][13][14][15][16]. One of these reactions is the organocatalytic asymmetric Michael reaction, which is a powerful synthetic method to generate new carbon-carbon bond with concomitant formation of a new stereogenic center [17][18][19][20][21][22][23]. Therefore, it can be applied in the synthesis of biologically important pharmaceuticals and chiral precursors for the synthesis of bioactive compounds (Fig.…”

Theoretical study on the reaction mechanisms of Michael chirality addition between propionaldehyde and nitroalkene catalyzed by an enantioselective catalyst

“…The researchers have witnessed an exponential growth in the field of organocatalysis. [4][5][6] However, a recent major breakthrough has been introduced by chiral metal catalysis for the stereoselective synthesis of optically active and metallo-fullerene derivatives. 7,8 A set of chiral metal complexes has also been reported by the supplement a stereodivergent synthesis of (fullero) pyrrolidines with complete control of the diastereo-and enantioselective outcome.…”

“…An important endeavor in the field of developing of a new effective chiral ligand and catalyst, which exhibits the high stereoselectivity and enantioselectivity with novel skeletons, continues to be a challenging goal for organic chemists. The researchers have witnessed an exponential growth in the field of organocatalysis . However, a recent major breakthrough has been introduced by chiral metal catalysis for the stereoselective synthesis of optically active and metallo‐fullerene derivatives .…”