Sila-rhubafuran and Derivatives: Synthesis and Olfactory Characterization of Novel Silicon-Containing Odorants

Forster, B. M.; Bertermann, Rüdiger; Kraft, Philip; Tacke, Reinhold

doi:10.1021/om401070c

Cited by 25 publications

(8 citation statements)

References 17 publications

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“…The absolute configuration was determined by comparison of the specific rotation with those of the literatures: , colorless oil; [α] 589 16.5 = +53.4 ( c 1.0, CHCl 3 ); R f = 0.71 ( n -hexane–EtOAc, 9:1); 1 H NMR (400 MHz, CDCl 3 ) 9.52 (1H, s), 7.41–7.24 (5H, m), 5.60–5.49 (1H, m), 5.09–5.02 (2H, m), 2.73–2.60 (2H, m), 1.45 (3H, s); 13 C{ 1 H} NMR (100 MHz, CDCl 3 ) 202.0, 139.4, 133.1, 128.8, 127.3, 127.1, 118.6, 53.6, 40.5, 18.8. Spectroscopic data of 4a – h , j , k , and 4m are in agreement with the published data.…”

Section: Methodssupporting

confidence: 89%

Organocatalytic Asymmetric α-Allylation and Propargylation of α-Branched Aldehydes with Alkyl Halides

Yoshida

2021

J. Org. Chem.

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Enantioselective α-allylation and -propargylation of α-branched aldehydes with alkyl halides was successfully performed using a chiral primary amino acid organocatalyst. This alkylation reaction, involving the generation of a chiral quaternary carbon stereocenter, proceeded smoothly in a mildly basic aqueous solution of potassium hydrogen carbonate to furnish α-allylated or -propargylated aldehydes in a good yield (up to 87%) and high enantioselectivity (up to 96% ee).

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Section: Methodssupporting

confidence: 89%

Organocatalytic Asymmetric α-Allylation and Propargylation of α-Branched Aldehydes with Alkyl Halides

Yoshida

2021

J. Org. Chem.

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“…Silahydrocarbons are sometimes encountered in pharmaceuticals and material chemistry 1 – 4 . Compared with all-carbon parent compounds, Si-element generally endows the corresponding hydrocarbons with unique biological activity and physical–chemical properties 5 – 8 , which are mainly determined by the different covalent radius and electronegativity of silicon from carbon. In these regards, arene-fused siloles have especially attracted many concerns due to their promising applications in electronic and optoelectronic devices 9 – 13 .…”

Section: Introductionmentioning

confidence: 99%

Photocatalyzed cycloaromatization of vinylsilanes with arylsulfonylazides

Chen

Shao

et al. 2021

Nat Commun

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Sila-molecules have recently attracted attention due to their promising applications in medical and industrial fields. Compared with all-carbon parent compounds, the different covalent radius and electronegativity of silicon from carbon generally endow the corresponding sila-analogs with unique biological activity and physicochemical properties. Vinylsilanes feature both silyl-hyperconjugation effect and versatile reactivities, developing vinylsilane-based Smiles rearrangement will therefore provide an efficient platform to assemble complex silacycles. Here we report a practical Ir(III)-catalyzed cycloaromatization of ortho-alkynylaryl vinylsilanes with arylsulfonyl azides for delivering naphthyl-fused benzosiloles under visible-light photoredox conditions. The combination of experiments and density functional theory (DFT) energy profiles reveals the reaction mechanism involving α-silyl radical Smiles rearrangement.

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“…The intramolecular hydroalkoxylation of linear alkene–alcohol substrates represents a general strategy for the construction of O -heterocycles, in which additional heteroatoms can be introduced to the tether between the two functional groups. With their continued interest in Si -containing fragrances, the Tacke group employed Lewis acid-catalyzed hydroalkoxylation for the synthesis of several analogs of rhubafuran with green and fruity notes [ 126 ] ( Scheme 11 a). A five-membered ring was formed when terminal alkenes were used, while substrates with internal double bonds led to a six-membered ring.…”

Section: Synthesis Of Heterocyclic Fragrances Via Addition-type React...mentioning

confidence: 99%

Synthesis of Cyclic Fragrances via Transformations of Alkenes, Alkynes and Enynes: Strategies and Recent Progress

Lin¹,

Huang²,

Ouyang³

et al. 2022

Molecules

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With increasing demand for customized commodities and the greater insight and understanding of olfaction, the synthesis of fragrances with diverse structures and odor characters has become a core task. Recent progress in organic synthesis and catalysis enables the rapid construction of carbocycles and heterocycles from readily available unsaturated molecular building blocks, with increased selectivity, atom economy, sustainability and product diversity. In this review, synthetic methods for creating cyclic fragrances, including both natural and synthetic ones, will be discussed, with a focus on the key transformations of alkenes, alkynes, dienes and enynes. Several strategies will be discussed, including cycloaddition, catalytic cyclization, ring-closing metathesis, intramolecular addition, and rearrangement reactions. Representative examples and the featured olfactory investigations will be highlighted, along with some perspectives on future developments in this area.

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Sila-rhubafuran and Derivatives: Synthesis and Olfactory Characterization of Novel Silicon-Containing Odorants

Cited by 25 publications

References 17 publications

Organocatalytic Asymmetric α-Allylation and Propargylation of α-Branched Aldehydes with Alkyl Halides

Organocatalytic Asymmetric α-Allylation and Propargylation of α-Branched Aldehydes with Alkyl Halides

Photocatalyzed cycloaromatization of vinylsilanes with arylsulfonylazides

Synthesis of Cyclic Fragrances via Transformations of Alkenes, Alkynes and Enynes: Strategies and Recent Progress

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