Chiral Sulfinamides as Highly Enantioselective Organocatalysts

Dinér, Peter; Sadhukhan, Arghya; Blomkvist, Björn

doi:10.1002/cctc.201402558

Cited by 29 publications

(15 citation statements)

References 29 publications

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“…It seems that the acidities and structures of receptors both affect the anion binding affinities. We proposed that the phenyl group might enhance the halide ions’ binding affinities of receptors through aryl C–H···anion interaction. ,, Considering the Lewis-base properties of the SO group, , the tert -butyl sulfinyl group may enhance the HSO 4 – binding affinities through the hydrogen-bonding interaction between the hydroxyl of the HSO 4 – anion and the SO group of the receptor.…”

Section: Resultsmentioning

confidence: 94%

N-tert-Butyl Sulfinyl Squaramide Receptors for Anion Recognition through Assisted tert-Butyl C–H Hydrogen Bonding

Yang

Shen

et al. 2017

J. Org. Chem.

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A series of novel N-tert-butyl sulfinyl squaramide receptors have been designed and synthesized. Their interactions with a range of inorganic anions were studied in solution by H NMR spectroscopy. This new type of squaramide displayed better anion-binding abilities over conventional diphenyl squaramides. The single crystal analysis and DFT calulations implied the role of the tert-butyl C-H protons in binding Cl. The energies of C-H···Cl interactions were estimated to be 1.4-1.6 kcal/mol in solution.

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Section: Resultsmentioning

confidence: 94%

N-tert-Butyl Sulfinyl Squaramide Receptors for Anion Recognition through Assisted tert-Butyl C–H Hydrogen Bonding

Yang

Shen

et al. 2017

J. Org. Chem.

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“…Considering chiral sulfinamide have been widely used as chiral auxiliaries, as ligands in transition-metal catalysis, and as organocatalysts [57][58][59][60] , we were interested of figuring out whether the corresponding sulfinamide can be obtained. To our delight, with the optimal reaction conditions, various enantiomerically enriched difluorosulfinamides were isolated after S N Ar reaction (Figure 5a).…”

Section: Difluoro(aminosulfinyl)methylationmentioning

confidence: 99%

Difluoromethyl 2-Pyridyl Sulfoximine: A Stereoselective Nucleophilic Reagent for Difluoro(aminosulfinyl)methylation and Difluoro(aminosulfonyl)methylation

Liu¹,

Ni²,

Wang³

et al. 2022

CCS Chem

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1,1-Difluorinated sulfonamides are known to have improved anti-inflammatory activity and enzyme inhibitory potency than their non-fluorinated counterparts, where two geminal fluorine atoms can give rise to electronic perturbation of the nearby polar groups and improve their biological activity. However, as methods for their stereoselective synthesis are scarce, such entities remain entirely unexplored. Here, we outline an efficient method for stereoselective introduction of difluoro(aminosulfonyl)methyl group (CF 2 SO 2 NH 2 ) into carbonyls, imines, and alkyl halides with a new (R)-2-pyridyl difluoromethyl sulfoximine reagent, which provides an unique solution for synthesis of chiral ,-difluorinated sulfonamides with a quaternary stereocenter. Its potency is illustrated by the synthesis of fluorinated analogues of bioactive compounds such as 2-OH-SA, one of antagonists for GABA B receptor in guinea pig ileum, and the late-stage modification of complex molecules such as haloperidol, ebastine, cholesterol and (+)--tocopherol derivatives.Stereoselective difluoro(aminosulfinyl)methylation to yield chiral sulfinylamides are presented, showcasing other uses of this new reagent.

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“…1 Several informative reviews have also appeared on the preparation and applications of sulnamides over the times. [9][10][11] Recently, our group contributed a review outlining the synthetic methods towards N-heterocycles mediated by tert-butanesulnamide. 12 The current review aims to discuss the application of aryl sul-nimines, majorly p-toluene sulnimine in the synthesis of Nheterocycles.…”

Section: Introductionmentioning

confidence: 99%

Applications of aryl-sulfinamides in the synthesis of N-heterocycles

et al. 2021

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Chiral Sulfinamides as Highly Enantioselective Organocatalysts

Abstract: Scheme 10. Catalysts used in the enantioselective Strecker reaction.Scheme 11. Organocatalysed epoxide ring-opening with anilines.

Cited by 29 publications

References 29 publications

N-tert-Butyl Sulfinyl Squaramide Receptors for Anion Recognition through Assisted tert-Butyl C–H Hydrogen Bonding

N-tert-Butyl Sulfinyl Squaramide Receptors for Anion Recognition through Assisted tert-Butyl C–H Hydrogen Bonding

Difluoromethyl 2-Pyridyl Sulfoximine: A Stereoselective Nucleophilic Reagent for Difluoro(aminosulfinyl)methylation and Difluoro(aminosulfonyl)methylation

Applications of aryl-sulfinamides in the synthesis of N-heterocycles

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