Titanium promoted reduction of imines with Grignards, silanes, and zinc: identification of a new mechanism with silanes

Kumar, Akshai; Pandiakumar, Arun Kumar; Samuelson, Ashoka G.

doi:10.1016/j.tet.2014.03.035

Cited by 5 publications

(2 citation statements)

References 32 publications

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“…Synthesis of PhSiD 3 . 25 LiAlD 4 (1.2 g, 31.22 mmol) was mixed with dry Et 2 O (100 mL) and cooled to 0 °C in an ice bath. Trichlorophenylsilane (2.5 mL, 15.61 mmol) was added slowly to the above suspension in a dropwise manner.…”

Section: ■ Experimental Sectionmentioning

confidence: 99%

Specific Z-Selectivity in the Oxidative Isomerization of Allyl Ethers to Generate Geometrically Defined Z-Enol Ethers Using a Cobalt(II)(salen) Complex Catalyst

Huang

Tao

et al. 2020

J. Org. Chem.

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Enol ether structural motifs exist in many highly oxygenated biologically active natural products and pharmaceuticals. The synthesis of the geometrically less stable Z-enol ethers is challenging. An efficient Z-selective oxidative isomerization process of allyl ethers catalyzed by a cobalt(II) (salen) complex using N-fluoro-2,4,6-trimethylpyridinium trifluoromethanesulfonate (Me3NFPY•OTf) as an oxidant has been developed. Thermodynamically less stable Z-enol ethers were prepared in excellent yields with high geometric control. This methodology also demonstrates the effectiveness in controlling the Z-selective isomerization reaction of diallyl ethers at room temperature. This catalytic system provides an alternative pathway to extend the traditional reductive isomerization of allyl ethers.

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Section: ■ Experimental Sectionmentioning

confidence: 99%

Specific Z-Selectivity in the Oxidative Isomerization of Allyl Ethers to Generate Geometrically Defined Z-Enol Ethers Using a Cobalt(II)(salen) Complex Catalyst

Huang

Tao

et al. 2020

J. Org. Chem.

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“…81 PhSiD3 was synthesized from the reaction of LiAlD4 and PhSiCl3 in diethyl ether. 82 Na and K were purchased as dispersions in mineral oil and they were washed with hexane.…”

Section: Methodsmentioning

confidence: 99%

Small Molecule Activation with Dinuclear Cobalt Complexes based on the Two-In-One Pincer Ligands

Li¹

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Oxidation and Reduction

Banerji¹

2017

Organic Reaction Mechanisms · 2014

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Titanium promoted reduction of imines with Grignards, silanes, and zinc: identification of a new mechanism with silanes

Cited by 5 publications

References 32 publications

Specific Z-Selectivity in the Oxidative Isomerization of Allyl Ethers to Generate Geometrically Defined Z-Enol Ethers Using a Cobalt(II)(salen) Complex Catalyst

Specific Z-Selectivity in the Oxidative Isomerization of Allyl Ethers to Generate Geometrically Defined Z-Enol Ethers Using a Cobalt(II)(salen) Complex Catalyst

Small Molecule Activation with Dinuclear Cobalt Complexes based on the Two-In-One Pincer Ligands

Oxidation and Reduction

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