2009
DOI: 10.1055/s-0029-1216796
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Organocatalytic Formation of Quaternary Stereocenters

Abstract: This work reviews the authors' choice of recently published papers where at least one asymmetric quaternary stereocenter has been formed via organocatalysis. The scope and limitations of the reactions are highlighted\ud 90% ee and >10 : 1 dr

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Cited by 548 publications
(137 citation statements)
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“…[1a-c,5] The construction of a highly hindered, strained spirocyclic quaternary chiral centre is in fact not a trivial task, especially in an enantioselective fashion. [6] In the last years, catalytic asymmetric cycloaddition [7] and cascade [8] reactions have proved to be amongst the most powerful approaches for the direct enantioselective assembly of the spirooxindole framework, starting from commercial or readily available compounds. These reports are however mostly limited to pyrrolidin-3-yl-spirooxindole motives resembling the natural spirotryprostatins, [7] or to all-carbon cycloalkyl-spirooxindoles.…”
mentioning
confidence: 99%
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“…[1a-c,5] The construction of a highly hindered, strained spirocyclic quaternary chiral centre is in fact not a trivial task, especially in an enantioselective fashion. [6] In the last years, catalytic asymmetric cycloaddition [7] and cascade [8] reactions have proved to be amongst the most powerful approaches for the direct enantioselective assembly of the spirooxindole framework, starting from commercial or readily available compounds. These reports are however mostly limited to pyrrolidin-3-yl-spirooxindole motives resembling the natural spirotryprostatins, [7] or to all-carbon cycloalkyl-spirooxindoles.…”
mentioning
confidence: 99%
“…Remarkably, tetrahydro-b-carboline spirooxindoles of type 4 are the core of some potent anti-malarial agents showing very good pharmacokinetic properties, recently discovered by intensive high throughput screening processes. [4] We started our optimisation (Table 1) by studying the reaction of tryptamine 2a with isatin 3a under the catalysis of several (S)-BINOL derived phosphoric acids 1a-f with different substituents at the 3 and 3' positions (Table 1 entries [1][2][3][4][5][6]. [9,11] THF was chosen as reaction medium to ensure solubilisation of isatin 3a.…”
mentioning
confidence: 99%
“…SOR-CHEM C. Palumbo and M. Guidotti: Organocatalysts for enantioselective synthesis of fine chemicals identified on the mechanistic basis: (i) covalent organocatalysis and (ii) non-covalent organocatalysis [26]. In the former case, within the catalytic cycle, the catalyst covalently binds the substrate, in the latter case only noncovalent interactions, such as hydrogen bonding (H-bonding) or the formation of ion pairs, activate the molecule towards the asymmetric transformation (Figure 4) [27]. With this brief review contribution, we would like to give a sketchy overview on both types of activation modes, subsequently focusing on some recent outcomes in the field of noncovalent organocatalysis.…”
Section: Definition and Origins Of Organocatalysismentioning
confidence: 99%
“…However, the obtainment of tetrasubstituted chiral carbons is, in general, a demanding task in organic chemistry [40]. Additionally, the preparation of chiral tertiary alcohols is potentially attractive for the synthesis of medicinal targets [41].…”
Section: Enantioselective Henry Reaction With Ketonesmentioning
confidence: 99%