Search results for " asymmetric synthesis"
showing 9 items of 9 documents
Recent progress in the application of fluorinated chiral sulfinimine reagents
2018
Abstract The development of synthetic methodology allowing for a strategic incorporation of fluorine into target compounds is in a high demand in many areas of the chemical and pharmaceutical industries. In this regard, application of fluorinated chiral sulfinimine reagents, in particularly, N-tert-butylsulfinyl-3,3,3-trifluoroacetaldimine, is one of the most general and practical approaches for preparation of compounds containing pharmacophoric fluoro-amino-keto/hydroxy moieties. This article provides a timely and comprehensive overview of the recent synthetic applications of fluorinated chiral sulfinimine reagents for asymmetric synthesis of fluoro-containing polyfunctional amino-compound…
Supported Organocatalysts: a Powerful Tool in Organic Synthesis
2012
ASYMMETRIC SYNTHESIS OF LINEZOLID THROUGH CATALYZED HENRY REACTION
2013
Linezolid 1 is an antibacterial oxazolidinone approved by FDA in 2000 for the treatment of fastidious bacterial infections.1 The asymmetric synthesis of Linezolid-like molecules make use of the chiral pool approach, through the so-called Manninen reaction.2 This strategy requires the use of BuLi, low temperature and a long elaboration of the acetamide chain. Curiously, the only catalyzed approach toward the asymmetrical synthesis of Linezolid was just recently reported, and belongs to the use of proline-derived catalysts in aldol reactions as the key step.3 This procedure is quite interesting except for the low yield. Here we report a new synthesis of Linezolid, based on a Cu(II)-catalyzed …
Scalable (Enantioselective) Syntheses of Novel 3-Methylated Analogs of Pazinaclone, (S)-PD172938 and Related Biologically Relevant Isoindolinones
2022
Herein, we report the application of an efficient and practical K2CO3 promoted cascade reaction of 2-acetylbenzonitrile in the synthesis of novel 3-methylated analogs of Pazinaclone and PD172938, belonging to isoindolinones heterocyclic class bearing a tetrasubstituted stereocenter. Organocatalytic asymmetric synthesis of the key intermediate and its transformation into highly enantioenriched 3-methylated analog of (S)-PD172938 was also developed. These achievements can be of particular interest also for medicinal chemistry, since the methyl group is a very useful structural modification in the rational design of new and more effective bioactive compounds.
Supported Organocatalysts as a Powerful Tool in Asymmetric Synthesis
2010
“Nonsolvent” Applications of Ionic Liquids in Organocatalysis
2012
This chapter is organized in three sections (see Figure 10.1 ): 2. Immobilization of ionic liquids and organocatalysts 2.1 Covalently attached “ ionic liquid ” moieties as supports 2.2 Covalently attached “ ionic liquid ” moieties as linkers 2.3 Covalently attached “ ionic liquid ” moieties as organocatalysts
Asymmetric Organocatalytic Synthesis of 4-Aminoisochromanones via a Direct One-Pot Intramolecular Mannich Reaction
2016
Synthesis 48(24), 4451 - 4458(2016). doi:10.1055/s-0035-1562522
Palladium Catalyzed [3+2] Cycloaddition of Vinyl Aziridine and Indane-1,3-diones: Diastereo- and Enantioselective Access to Spiro-Pyrrolidines
2020
A mild and efficient palladium-catalyzed [3+2] cycloaddition of vinylaziridine and indane-1,3-diones has been realized. The resulting spiro-pyrrolidines were provided in excellent yields and, with the introduction of the leucine-derived phosphine ligand, moderate to good enantio- and diastereoselectivities.
Advantages in supporting chiral organocatalysts
2010
An overview on the advances in supporting organocatalysts for their use and recycle in the asymmetric synthesis is presented, focusing on the main approaches for the immobilization and highlighting those examples in which supported and unsupported version of the catalyst behave similarly and high level of recyclability have been obtained.