Synthesis and X-ray crystal structure of a chiral molybdenum porphyrin and its catalytic behaviour toward asymmetric epoxidation of aromatic alkenes

Liu, Weisheng; Zhang, Rui; Huang, Jie‐Sheng; Che, Chi‐Ming; Peng, Shie‐Ming

doi:10.1016/s0022-328x(01)01075-0

Cited by 20 publications

(1 citation statement)

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“…As a result the potential of such complexes as enantioselective catalysts is reduced and they can also have a low stability [14]. The same problems seem to hamper the successful application of Mo-porphyrin catalysts in asymmetric olefin epoxidation [15].…”

Section: Introductionmentioning

confidence: 99%

Synthesis, characterization and catalytic studies of bis(chloro)dioxomolybdenum(VI)-chiral diimine complexes

Gago

Rodríguez‐Borges

Teixeira

et al. 2005

Journal of Molecular Catalysis A: Chemical

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Section: Introductionmentioning

confidence: 99%

Synthesis, characterization and catalytic studies of bis(chloro)dioxomolybdenum(VI)-chiral diimine complexes

Gago

Rodríguez‐Borges

Teixeira

et al. 2005

Journal of Molecular Catalysis A: Chemical

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Catalytic Enantioselective Reactions using Organomanganese Compounds

Chinkov

2011

Patai's Chemistry of Functional Groups

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The use of organomanganese reagents in asymmetric catalysis represents an attractive niche for synthetic chemists mainly due to the toxicological benignancy and low cost. Yet, the arsenal of the existing organomanganese catalysts, processes and substrates used in the enantioselective reactions is quite limited. This chapter covers the chief achievements made within the last quarter of a century in this area. The majority of the transformations are made by the Mn III ‐salen compounds, which are commonly used as potent oxene‐ and nitrene‐transfer agents in the epoxidation and aziridination reactions of CC bonds. The scope, limitations and mechanistic studies of these processes are discussed. Additional class of transformations performed by the Mn III ‐salen is asymmetric hydroxylation and amination of CH bonds as well as formation of SO and SN in sulfides. Less common Mn‐porphyrin and other scarcely studied complexes and their corresponding asymmetric reactions are discussed as well.

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3‐ and 4‐Uloses Derived from N‐Acetyl‐D‐glucosamine: A Unique Pair of Complementary Organocatalysts for Asymmetric Epoxidation of Alkenes

Schöberl

Jäger

2012

Adv Synth Catal

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The 4-ulose and the 3-ulose, both derived in two steps from the a-methyl glycoside of Nacetyl-d-glucosamine (GlcNAc), act as organocatalysts in the asymmetric epoxidation of alkenes, with unprecedented complementary enantioselectivity. The best results are found with a,b-unsaturated esters as substrates, with enantiomeric ratios up to 90:10 and 11:89, respectively.Typical Epoxidation Protocol, trans-1-Acetoxy-2,3epoxy-3-phenylpropane (Table 2, entry 5) Cinnamyl acetate (88.1 mg, 0.50 mmol) was dissolved in acetonitrile and aqueous Na 2 EDTA solution (10 À4 M, 2 mL each) and Bu 4 NHSO 4 (15 mg) were added with vigorous stirring at 28 8C. A small portion of a mixture of oxone (1.537 g, 2.5 mmol) and NaHCO 3 (0.651 g, 7.75 mmol) was added to the mixture to bring the pH to > 7. Then the 4-Scheme 4. Overall yields of the catalysts 5 and 6. 794

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Synthesis and X-ray crystal structure of a chiral molybdenum porphyrin and its catalytic behaviour toward asymmetric epoxidation of aromatic alkenes

Cited by 20 publications

References 20 publications

Synthesis, characterization and catalytic studies of bis(chloro)dioxomolybdenum(VI)-chiral diimine complexes

Synthesis, characterization and catalytic studies of bis(chloro)dioxomolybdenum(VI)-chiral diimine complexes

Catalytic Enantioselective Reactions using Organomanganese Compounds

3‐ and 4‐Uloses Derived from N‐Acetyl‐D‐glucosamine: A Unique Pair of Complementary Organocatalysts for Asymmetric Epoxidation of Alkenes

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