Übergangsmetall‐katalysierte Reaktionen von ungesättigten α‐Diazo‐α‐(trimethylsilyl)essigestern mit Carbonylverbindungen

Alt, Mechthild; Maas, Gerhard

doi:10.1002/cber.19941270831

Cited by 25 publications

(5 citation statements)

References 23 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…The reaction of compound 7a with acetone led to enol adduct 14a in 55% yield. A similar reaction was reported by Alt and Maas in 1994, in the presence of a rhodium catalyst and by Crocker et al under photochemical conditions …”

Section: Photochemical Reactivity Of Diazo Compounds 7 In Nonhalogena...supporting

confidence: 87%

Unique Reactivity of Triazolyl Diazoacetates under Photochemical Conditions

Wosińska-Hrydczuk,

Yaghoobi Anzabi,

Przeździecki

et al. 2024

ACS Org. Inorg. Au

View full text Add to dashboard Cite

Under light irradiation, aryldiazo acetates can generate either singlet or triplet carbenes depending on the reaction conditions, but heteroaryl diazo compounds have remained underexplored in this context. Herein, we found that triazolyl diazoacetates exhibit higher reactivity than their aryl counterparts. They even react with dichloromethane (DCM), a common, inert solvent, for photoreactions involving diazo reagents, giving halogenated products. Theoretical studies show that all reactions involve carbenes but progress via different pathways depending on the solvent used.

show abstract

Section: Photochemical Reactivity Of Diazo Compounds 7 In Nonhalogena...supporting

confidence: 87%

Unique Reactivity of Triazolyl Diazoacetates under Photochemical Conditions

Wosińska-Hrydczuk,

Yaghoobi Anzabi,

Przeździecki

et al. 2024

ACS Org. Inorg. Au

View full text Add to dashboard Cite

show abstract

“…Retention time: 3.5 min for ent-6a, 3.8 min for 6a;[α] D 21 +58 (c 0.63, 94% ee, CHCl 3 ). The spectroscopic data are consistent with the reported data 2). according to Procedure B and was obtained as a yellow oil (59%, 79% ee,when tetrakis(acetonitrile)copper(I)tetrafluoroborate and L2 were used.…”

supporting

confidence: 88%

Catalytic Asymmetric Intramolecular Cyclopropanation of α-Diazo-α-Silyl Acetate

Inoue

Nagatani

Tezuka

et al. 2017

Synlett

View full text Add to dashboard Cite

General Information. 1 H and 13 C NMR spectra were recorded on a JEOL AL-400 spectrometer or a JEOL ECZ500R spectrometer. Chemical shifts are reported in ppm with the residual solvent resonance as internal standard (CDCl 3 1 H, δ = 7.26 ppm, 13 C, δ = 77.16 ppm). The following abbreviations were used to explain the multiplicities: s, singlet; d, doublet; t, triplet; q, quartet; m, multiplet; sep, septet; br, broad. IR spectra were recorded on a JASCO FT/IR-8300. Optical rotations were measured using a 2 ml cell with a 1 dm path length on a JASCO DIP-1000. Mass spectra and elemental analyses were provided at the Materials Characterization Central Laboratory, Waseda University. All reactions were carried out under an argon atmosphere with dry, freshly distilled solvents under anhydrous conditions, unless otherwise noted. Melting point (mp) is uncorrected, recorded on a Yamato capillary melting point apparatus. Chiral HPLC analysis was performed on a JASCO PU-980 and UV-970 detector. Chiral gas chromatography analysis was performed on capillary column RT-γ-DEXsm, SUPELCO, 30 m×0.25 mm×0.25 μm at 150 °C constant, pressure: 138 kPa, column flow amount: 2.50 ml/min, line speed: 53.9 m/s, ratio of sprit: 40.0, total flow amount: 106 ml/min, SPRIT, and career gas was He. All reactions were monitored by thin-layer chromatography carried out on 0.25 mm E. Merck silica gel plates (60F-254) using UV light as visualizing agent and phosphomolybdic acid and heat as developing agents. E. Kanto Chemical Silica Gel 60N (spherical, neutral, 63-210 μm or 40-50 μm partial size) was used for flash chromatography. Preparative thin-layer chromatography (PTLC) separations were carried out on self-made 0.3 mm E. Merck silica gel plates (60F-254). TLC Rfs of purified compounds were included. Materials. THF and Et 2 O were distilled from sodium/benzophenone ketyl, and CH 2 Cl 2 , benzene, and hexane from calcium hydride. DMF and DMSO were distilled from calcium hydride under reduced pressure. Toluene and EtOH were distilled from sodium. MeOH was distilled from magnesium and I 2. All reagents were purchased from Aldrich, TCI, Merck, or Kanto Chemical Co. Ltd.

show abstract

“…29 The reactions of allyl or 3-butenyl R-diazo-R-(trimethylsilyl)acetates 59a,b with aldehydes or acetone under catalysis of rhodium perfluorobutyrate or copper triflate afforded several different types of products. 30 When the interaction of allyl R-diazo-R-(trimethylsilyl)acetates 59a with an aldehyde was carried out in the presence of rhodium perfluorobutyrate, the only isolated products were the [1 + 1]-adducts, 5-allyl-5-trimethylsilyl-1,3-dioxolan-4ones 60. If the same reaction was catalyzed by copper triflate, three heterocyclic compounds (61-63) were obtained.…”

Section: Silicon-substituted Carbenesmentioning

confidence: 99%