Dithioacetal as a 1,1-zwitterion synthon. Synthesis of functionalized alkenes by the coupling of benzylic dithioacetals with another 1,1-zwitterion synthon

Tu, Haiyang; Liu, Yi-Hung; Yu, Wei; Luh, Tien‐Yau

doi:10.1016/j.tetlet.2004.12.016

Cited by 7 publications

(4 citation statements)

References 18 publications

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“…Coupling reactions are the most common approach to desired enynes; however, it is necessary to use expensive noble transition metals . Functionalized enynes can also be synthesized by sequential reaction of propargylic dithioacetal with butyllithium and α-bromo esters followed by treatment with alumina . The [2 + 2] cycloaddition of an alkynyl ketone with a ynolate and subsequent electrocyclic reaction leads to enyne compounds bearing a carbonyl group .…”

Section: Resultsmentioning

confidence: 99%

“…13 Functionalized enynes can also be synthesized by sequential reaction of propargylic dithioacetal with butyllithium and α-bromo esters followed by treatment with alumina. 14 The [2 + 2] cycloaddition of an alkynyl ketone with a ynolate and subsequent electrocyclic reaction leads to enyne compounds bearing a carbonyl group. 15 In addition, functionalized enynes are also formed by oxidation of βfunctionalized semicarbazones with selenium dioxide.…”

Section: ■ Results and Discussionmentioning

confidence: 99%

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Alkynylation and Cyanation of Alkenes Using Diverse Properties of a Nitro Group

et al. 2018

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In the work being reported here, β-nitrostyrenes bearing an ethoxycarbonyl group at the β-position serve as scaffolds for the synthesis of α,β-difunctionalized alkenes. Nitrocinnamates undergo Michael addition reactions with versatile sp3- and sp2-nucleophiles such as alcohols, Grignard reagents, alkylcopper, and dialkylzinc to afford β-substituted nitroethane derivatives. However, various attempts to obtain a double bond via nitrous acid elimination failed because steric repulsion between the newly introduced sp3/sp2 substituent and the nitro group hampered the required anti-coplanar conformation. This problem was successfully overcome using a smaller sp-nucleophile such as lithium acetylide, potassium cyanide, or trimethylsilyl cyanide. While treatment of the adduct with a strong base did not lead to the elimination of nitrous acid, the weaker triethylamine efficiently afforded functionalized enynes and acrylonitriles in high yields.

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Section: Resultsmentioning

confidence: 99%

Section: ■ Results and Discussionmentioning

confidence: 99%

Alkynylation and Cyanation of Alkenes Using Diverse Properties of a Nitro Group

et al. 2018

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“…The spectral data obtained for known compounds 1-8, 11-12, 14-16 are agreement with the data published in the literature. [20][21][22][23][24][25][26][27][28][29][30][31][32] General Procedure for the Nitration with NaNO 2…”

Section: Experimental Section General Procedures For the Nitration Witmentioning

confidence: 99%

A Selective and Practical Synthesis of Nitroolefins

Jovel¹,

Prateeptongkum²,

Jackstell³

et al. 2008

Adv Synth Catal

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“…[37] It is envisaged that the thioether moiety in 14 may serve as a leaving group such that functionalized olefins 24 might be obtained when such functionalized alkyl halides are used in the reaction shown in Equation ( 17). [38] It is interesting to note that ester group in 23 is stable under the reaction conditions.…”

Section: Propargylic Dithioacetals As 33-propyne Zwitterion Equivalentsmentioning

confidence: 99%