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Papers by Simona Petrželová

Research paper thumbnail of CCDC 2212693: Experimental Crystal Structure Determination

The Cambridge Structural Database, 2023

Research paper thumbnail of Synthesis of enantiopure 1,2,3-triazolylidene-type mesoionic carbene (MIC) conjugate acids featuring a rigid bicyclic scaffold

Organic chemistry frontiers, 2024

Research paper thumbnail of Integrating Computational Chemistry into Secondary School Lessons

Journal of chemical education, May 21, 2024

Research paper thumbnail of Access to Spirooxindole-Fused Cyclopentanes via a Stereoselective Organocascade Reaction Using Bifunctional Catalysis

Journal of Organic Chemistry, Jan 27, 2023

The present study reports an asymmetric organocascade reaction of oxindole-derived alkenes with 3... more The present study reports an asymmetric organocascade reaction of oxindole-derived alkenes with 3-bromo-1nitropropane efficiently catalyzed by the bifunctional catalyst. Spirooxindole-fused cyclopentanes were produced in moderate-togood isolated yields (15-69%) with excellent stereochemical outcomes. The synthetic utility of the protocol was exemplified on a set of additional transformations of the corresponding spirooxidondole compounds. 1 C1 K2CO3 24 17/1 58 99 2 C2 K2CO3 24 3/1 39 92 3 C3 K2CO3 24 3/1 58 91 4 C1 Na2CO3 48 20/1 55 99 5 C1 NaHCO3 168 20/1 32 99 6 C1 DIPEA 24 2/1 49 98 7 e C1 K2CO3 2 3/1 38 91 8 f C1 K2CO3 3 8/1 23 99 9 g C1 K2CO3 24 >20/1 59 99 10 h C1 K2CO3 18 >20/1 57 99 11 i C1 K2CO3 45 >20/1 64 99 a Reactions were conducted with 1a (0.1 mmol), 2a (0.2 mmol), corresponding base (0.2 mmol), and catalyst (20 mol%) in DCM (1.0 ml) at room temperature. b Determined by 1 H-NMR of the crude reaction mixture (3a/4a). c Isolated yield of 3a after column chromatography. d Determined by chiral HPLC analysis. e EtOAc was used. f MTBE was used. g CHCl3 was used. h Reaction was conducted with 1a (0.10 mmol), 3a (0.15 mmol), C1 (20 mol%) in CHCl3 (1.0 ml) at room temperature. i Reaction was conducted with 1a (0.10 mmol), 3a (0.15 mmol), C1 (1 mol%) in CHCl3 (1.0 ml) at room temperature.

Research paper thumbnail of Access to Spirooxindole-fused Cyclopentanes via Stereoselective Organocascade Reaction using Bifunctional Catalysis

The present study reports an asymmetric organocascade reaction of oxindole-derived alkenes with 3... more The present study reports an asymmetric organocascade reaction of oxindole-derived alkenes with 3-bromo-1nitropropane efficiently catalyzed by the bifunctional catalyst. Spirooxindole-fused cyclopentanes were produced in moderate-togood isolated yields (15-69%) with excellent stereochemical outcomes. The synthetic utility of the protocol was exemplified on a set of additional transformations of the corresponding spirooxidondole compounds. 1 C1 K2CO3 24 17/1 58 99 2 C2 K2CO3 24 3/1 39 92 3 C3 K2CO3 24 3/1 58 91 4 C1 Na2CO3 48 20/1 55 99 5 C1 NaHCO3 168 20/1 32 99 6 C1 DIPEA 24 2/1 49 98 7 e C1 K2CO3 2 3/1 38 91 8 f C1 K2CO3 3 8/1 23 99 9 g C1 K2CO3 24 >20/1 59 99 10 h C1 K2CO3 18 >20/1 57 99 11 i C1 K2CO3 45 >20/1 64 99 a Reactions were conducted with 1a (0.1 mmol), 2a (0.2 mmol), corresponding base (0.2 mmol), and catalyst (20 mol%) in DCM (1.0 ml) at room temperature. b Determined by 1 H-NMR of the crude reaction mixture (3a/4a). c Isolated yield of 3a after column chromatography. d Determined by chiral HPLC analysis. e EtOAc was used. f MTBE was used. g CHCl3 was used. h Reaction was conducted with 1a (0.10 mmol), 3a (0.15 mmol), C1 (20 mol%) in CHCl3 (1.0 ml) at room temperature. i Reaction was conducted with 1a (0.10 mmol), 3a (0.15 mmol), C1 (1 mol%) in CHCl3 (1.0 ml) at room temperature.

Research paper thumbnail of Access to Spirooxindole-Fused Cyclopentanes via a Stereoselective Organocascade Reaction Using Bifunctional Catalysis

Journal of Organic Chemistry, Jan 27, 2023

The present study reports an asymmetric organocascade reaction of oxindole-derived alkenes with 3... more The present study reports an asymmetric organocascade reaction of oxindole-derived alkenes with 3-bromo-1nitropropane efficiently catalyzed by the bifunctional catalyst. Spirooxindole-fused cyclopentanes were produced in moderate-togood isolated yields (15-69%) with excellent stereochemical outcomes. The synthetic utility of the protocol was exemplified on a set of additional transformations of the corresponding spirooxidondole compounds. 1 C1 K2CO3 24 17/1 58 99 2 C2 K2CO3 24 3/1 39 92 3 C3 K2CO3 24 3/1 58 91 4 C1 Na2CO3 48 20/1 55 99 5 C1 NaHCO3 168 20/1 32 99 6 C1 DIPEA 24 2/1 49 98 7 e C1 K2CO3 2 3/1 38 91 8 f C1 K2CO3 3 8/1 23 99 9 g C1 K2CO3 24 >20/1 59 99 10 h C1 K2CO3 18 >20/1 57 99 11 i C1 K2CO3 45 >20/1 64 99 a Reactions were conducted with 1a (0.1 mmol), 2a (0.2 mmol), corresponding base (0.2 mmol), and catalyst (20 mol%) in DCM (1.0 ml) at room temperature. b Determined by 1 H-NMR of the crude reaction mixture (3a/4a). c Isolated yield of 3a after column chromatography. d Determined by chiral HPLC analysis. e EtOAc was used. f MTBE was used. g CHCl3 was used. h Reaction was conducted with 1a (0.10 mmol), 3a (0.15 mmol), C1 (20 mol%) in CHCl3 (1.0 ml) at room temperature. i Reaction was conducted with 1a (0.10 mmol), 3a (0.15 mmol), C1 (1 mol%) in CHCl3 (1.0 ml) at room temperature.

Research paper thumbnail of Access to Spirooxindole-fused Cyclopentanes via Stereoselective Organocascade Reaction using Bifunctional Catalysis

The present study reports an asymmetric organocascade reaction of oxindole-derived alkenes with 3... more The present study reports an asymmetric organocascade reaction of oxindole-derived alkenes with 3-bromo-1-nitropropane efficiently catalyzed by the bifunctional catalyst. Spirooxindole-fused cyclopentanes were produced in moderate-to-good isolated yields (15-69%) with excellent stereochemical outcomes. The synthetic utility of the protocol was exemplified on a set of additional transformations of the corresponding spirooxidondole compounds.

Research paper thumbnail of Enantioselective Cyclopropanation of 4-Nitroisoxazole Derivatives

Advanced Synthesis & Catalysis

Research paper thumbnail of CCDC 2212693: Experimental Crystal Structure Determination

The Cambridge Structural Database, 2023

Research paper thumbnail of Synthesis of enantiopure 1,2,3-triazolylidene-type mesoionic carbene (MIC) conjugate acids featuring a rigid bicyclic scaffold

Organic chemistry frontiers, 2024

Research paper thumbnail of Integrating Computational Chemistry into Secondary School Lessons

Journal of chemical education, May 21, 2024

Research paper thumbnail of Access to Spirooxindole-Fused Cyclopentanes via a Stereoselective Organocascade Reaction Using Bifunctional Catalysis

Journal of Organic Chemistry, Jan 27, 2023

The present study reports an asymmetric organocascade reaction of oxindole-derived alkenes with 3... more The present study reports an asymmetric organocascade reaction of oxindole-derived alkenes with 3-bromo-1nitropropane efficiently catalyzed by the bifunctional catalyst. Spirooxindole-fused cyclopentanes were produced in moderate-togood isolated yields (15-69%) with excellent stereochemical outcomes. The synthetic utility of the protocol was exemplified on a set of additional transformations of the corresponding spirooxidondole compounds. 1 C1 K2CO3 24 17/1 58 99 2 C2 K2CO3 24 3/1 39 92 3 C3 K2CO3 24 3/1 58 91 4 C1 Na2CO3 48 20/1 55 99 5 C1 NaHCO3 168 20/1 32 99 6 C1 DIPEA 24 2/1 49 98 7 e C1 K2CO3 2 3/1 38 91 8 f C1 K2CO3 3 8/1 23 99 9 g C1 K2CO3 24 >20/1 59 99 10 h C1 K2CO3 18 >20/1 57 99 11 i C1 K2CO3 45 >20/1 64 99 a Reactions were conducted with 1a (0.1 mmol), 2a (0.2 mmol), corresponding base (0.2 mmol), and catalyst (20 mol%) in DCM (1.0 ml) at room temperature. b Determined by 1 H-NMR of the crude reaction mixture (3a/4a). c Isolated yield of 3a after column chromatography. d Determined by chiral HPLC analysis. e EtOAc was used. f MTBE was used. g CHCl3 was used. h Reaction was conducted with 1a (0.10 mmol), 3a (0.15 mmol), C1 (20 mol%) in CHCl3 (1.0 ml) at room temperature. i Reaction was conducted with 1a (0.10 mmol), 3a (0.15 mmol), C1 (1 mol%) in CHCl3 (1.0 ml) at room temperature.

Research paper thumbnail of Access to Spirooxindole-fused Cyclopentanes via Stereoselective Organocascade Reaction using Bifunctional Catalysis

The present study reports an asymmetric organocascade reaction of oxindole-derived alkenes with 3... more The present study reports an asymmetric organocascade reaction of oxindole-derived alkenes with 3-bromo-1nitropropane efficiently catalyzed by the bifunctional catalyst. Spirooxindole-fused cyclopentanes were produced in moderate-togood isolated yields (15-69%) with excellent stereochemical outcomes. The synthetic utility of the protocol was exemplified on a set of additional transformations of the corresponding spirooxidondole compounds. 1 C1 K2CO3 24 17/1 58 99 2 C2 K2CO3 24 3/1 39 92 3 C3 K2CO3 24 3/1 58 91 4 C1 Na2CO3 48 20/1 55 99 5 C1 NaHCO3 168 20/1 32 99 6 C1 DIPEA 24 2/1 49 98 7 e C1 K2CO3 2 3/1 38 91 8 f C1 K2CO3 3 8/1 23 99 9 g C1 K2CO3 24 >20/1 59 99 10 h C1 K2CO3 18 >20/1 57 99 11 i C1 K2CO3 45 >20/1 64 99 a Reactions were conducted with 1a (0.1 mmol), 2a (0.2 mmol), corresponding base (0.2 mmol), and catalyst (20 mol%) in DCM (1.0 ml) at room temperature. b Determined by 1 H-NMR of the crude reaction mixture (3a/4a). c Isolated yield of 3a after column chromatography. d Determined by chiral HPLC analysis. e EtOAc was used. f MTBE was used. g CHCl3 was used. h Reaction was conducted with 1a (0.10 mmol), 3a (0.15 mmol), C1 (20 mol%) in CHCl3 (1.0 ml) at room temperature. i Reaction was conducted with 1a (0.10 mmol), 3a (0.15 mmol), C1 (1 mol%) in CHCl3 (1.0 ml) at room temperature.

Research paper thumbnail of Access to Spirooxindole-Fused Cyclopentanes via a Stereoselective Organocascade Reaction Using Bifunctional Catalysis

Journal of Organic Chemistry, Jan 27, 2023

The present study reports an asymmetric organocascade reaction of oxindole-derived alkenes with 3... more The present study reports an asymmetric organocascade reaction of oxindole-derived alkenes with 3-bromo-1nitropropane efficiently catalyzed by the bifunctional catalyst. Spirooxindole-fused cyclopentanes were produced in moderate-togood isolated yields (15-69%) with excellent stereochemical outcomes. The synthetic utility of the protocol was exemplified on a set of additional transformations of the corresponding spirooxidondole compounds. 1 C1 K2CO3 24 17/1 58 99 2 C2 K2CO3 24 3/1 39 92 3 C3 K2CO3 24 3/1 58 91 4 C1 Na2CO3 48 20/1 55 99 5 C1 NaHCO3 168 20/1 32 99 6 C1 DIPEA 24 2/1 49 98 7 e C1 K2CO3 2 3/1 38 91 8 f C1 K2CO3 3 8/1 23 99 9 g C1 K2CO3 24 >20/1 59 99 10 h C1 K2CO3 18 >20/1 57 99 11 i C1 K2CO3 45 >20/1 64 99 a Reactions were conducted with 1a (0.1 mmol), 2a (0.2 mmol), corresponding base (0.2 mmol), and catalyst (20 mol%) in DCM (1.0 ml) at room temperature. b Determined by 1 H-NMR of the crude reaction mixture (3a/4a). c Isolated yield of 3a after column chromatography. d Determined by chiral HPLC analysis. e EtOAc was used. f MTBE was used. g CHCl3 was used. h Reaction was conducted with 1a (0.10 mmol), 3a (0.15 mmol), C1 (20 mol%) in CHCl3 (1.0 ml) at room temperature. i Reaction was conducted with 1a (0.10 mmol), 3a (0.15 mmol), C1 (1 mol%) in CHCl3 (1.0 ml) at room temperature.

Research paper thumbnail of Access to Spirooxindole-fused Cyclopentanes via Stereoselective Organocascade Reaction using Bifunctional Catalysis

The present study reports an asymmetric organocascade reaction of oxindole-derived alkenes with 3... more The present study reports an asymmetric organocascade reaction of oxindole-derived alkenes with 3-bromo-1-nitropropane efficiently catalyzed by the bifunctional catalyst. Spirooxindole-fused cyclopentanes were produced in moderate-to-good isolated yields (15-69%) with excellent stereochemical outcomes. The synthetic utility of the protocol was exemplified on a set of additional transformations of the corresponding spirooxidondole compounds.

Research paper thumbnail of Enantioselective Cyclopropanation of 4-Nitroisoxazole Derivatives

Advanced Synthesis & Catalysis