S-Ethenylsulfoximine derivatives. Reagents for ethylenation of protic nucleophiles

Johnson, Carl R.; Lockard, James P.; Kennedy, Eugene R.

doi:10.1021/jo01290a012

Cited by 50 publications

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“…The ethylenebridged derivative 9 had been synthesized by Johnson 1980 as a vinylsulfoximine precursor [49] and 10 was prepared as early as 1954 in 9% yield to explore the suspected intrinsic toxicity of the sulfoximine group. [50] The target C 1 -bridged bis(sulfoximine)s comprise a class of hitherto unknown compounds.…”

Section: Resultsmentioning

confidence: 99%

Geminal Bis(sulfoximine)s: Synthesis and Applications in Asymmetric Catalysis

2004

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A number of C 2 -symmetrical geminal bis-(sulfoximine)s have been prepared for the first time and used as ligands in boron-mediated reductions of acetophenone and copper complex-catalyzed 1,4-additions of diethylzinc to 2-cyclohexenone. The copper complex of bis(sulfoximine) 46 was found to be highly active in this type of reaction, furnishing the addition product in nearly quantitative yield even at À 90 8C. From the reaction of bis(sulfoximine) 42 with Cu(OTf) 2 a copper complex was isolated and characterized by X-ray structural analysis. A mixture of SES-Cl and NaN 3 in acetonitrile was found to behave like SES-N 3 in FeCl 2 -mediated iminations of sulfoxides, affording the corresponding sulfoximines with complete retention of the sulfur configuration.

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Section: Resultsmentioning

confidence: 99%

Geminal Bis(sulfoximine)s: Synthesis and Applications in Asymmetric Catalysis

2004

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“…5–7 Sulfoxonium salt 2a and all related racemic salts in this study were prepared by procedures previously described by Johnson and co-workers, while enantioenriched salts were prepared through an additional step, involving a resolution procedure described by Gais and co-workers. 6,7 …”

Section: Resultsmentioning

confidence: 99%

“…

{[α]}_{D}^{24 ° C}

= +4.35 (c = 6.85, CH 2 Cl 2 ) 6c ; IR (thin film): 1057 (BF stretch), 753 cm −1 ; 1 H NMR (400 MHz, CDCl 3 , TMS) for the major diastereomer: δ 8.34–8.32 (m, 2H), 7.98 (d, J = 15.08 Hz, 1H), 7.90–7.79 (m, 6H), 7.57–7.46 (m, 3H), 3.14 (s, 6H); 13 C NMR (100 MHz, CDCl 3 ) for the major diastereomer: δ 154.0, 137.2, 134.2, 131.6, 131.0, 130.9, 130.3, 129.8, 129.4, 115.7, 38.0; (M + ) HRMS m/z calcd for C 16 H 18 NOS + : 272.1109; found: 272.1111.…”

Section: Methodsmentioning

confidence: 99%

Asymmetric Synthesis of γ-Lactones through Koga Amine-Controlled Addition of Enediolates to α,β-Unsaturated Sulfoxonium Salts

et al. 2016

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A chiral Koga amine-controlled asymmetric synthesis of cis-γ-lactones through a formal [3 + 2] cycloaddition of enediolates with α,β-unsaturated sulfoxonium salts is described. The desired structural motif was formed in moderate to good yields (50–71% for 13 examples), with good to very good diastereoselectivity (dr 5:1 to 10:1 for 20 examples), favoring the cis-isomer, and good to excellent enantioselectivity (70–91% ee for 13 examples).

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“…8-diazabicyclo[5.4.0]undec-7-ene (DBU) furnished the corresponding alkenyl sulfoximines 6-9 as E-isomers in 85-92 % yield. [27,28] …”

Section: Acyclic Alkenyl Sulfoximinesmentioning

confidence: 99%

Synthesis of Phosphanyl Sulfoximines Through Phospha‐Michael Reaction of Alkenyl Sulfoximines and Their Evaluation as Chiral Bidentate 1,5‐N,P Ligands for Palladium in Asymmetric Allylic Alkylation

et al. 2010

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The intermolecular phospha-Michael reaction of cyclic and acyclic alkenyl sulfoximines proceeds readily and yields the corresponding phosphanyl sulfoximines in good yield. The asymmetric induction provided by sulfoximine group in C-P bond formation is apparently only low. The configuration of three phosphanyl sulfoximine-boranes has been determined by X-ray crystal structure analysis. The ability of the phosphanyl sulfoximines to act as ligand in Pd-catalyzed asymmetric allylic alkylation was studied with pairs of diastereomeric cyclic and acyclic derivatives carrying different substituents at the N atom. This study showed that the substituent at the N atom and both the chirality of the backbone and sulfoximine group play a crucial role in determining the enantioselectivity of the allylic alkylation. The Pd-catalyzed reaction of the racemic 1,3-diphenylallyl acetate with the mal-

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S-Ethenylsulfoximine derivatives. Reagents for ethylenation of protic nucleophiles

Cited by 50 publications

References 0 publications

Geminal Bis(sulfoximine)s: Synthesis and Applications in Asymmetric Catalysis

Geminal Bis(sulfoximine)s: Synthesis and Applications in Asymmetric Catalysis

Asymmetric Synthesis of γ-Lactones through Koga Amine-Controlled Addition of Enediolates to α,β-Unsaturated Sulfoxonium Salts

Synthesis of Phosphanyl Sulfoximines Through Phospha‐Michael Reaction of Alkenyl Sulfoximines and Their Evaluation as Chiral Bidentate 1,5‐N,P Ligands for Palladium in Asymmetric Allylic Alkylation

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