Browsing by Author "Deng, Jie-Cheng"

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[3+2] Cycloaddition of Dialkyl (E)-Hex-2-en-4-ynedioates to [60]Fullerene by Phosphane-Promoted Tandem alpha(delta ')-Michael Additions
(2012-05-01)
Chuang, Shih-Ching
;
Deng, Jie-Cheng
;
Chan, Fu-Wei
;
Chen, Sheng-Yuan
;
Huang, Wei-Je
Organophosphanes promote the [3+2] cycloaddition reactions of dialkyl (E)-hex-2-en-4-ynedioates and [60]fullerene, giving a series of cyclopenteno-fullerenes 3ak bearing phosphorus ylides. This cycloaddition reaction is initiated by the attack of nucleophilic phosphanes at the a(d')-C atom of the dialkyl (E)-hex-2-en-4-ynedioate, which generates a 1,3-dipolar species. These 1,3-dipoles then react with C60 followed by intramolecular cyclization to give cyclopenteno-fullerenes in moderate-to-good yields. In a cyclic voltmmetry study, these novel fullerenes show a larger cathodic shift in their first reduction potential relative to [6,6]phenyl-C61 methyl butyrate, which indicates that these new derivatives possess higher LUMO energy levels.
Access to oxindoles, isatins, and isoxazolinones via multicomponent reactions and facile 6 pi electrocyclization
(2015-08-16)
Chuang, Shih-Ching
;
Deng, Jie-Cheng
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應用化學系
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Department of Applied Chemistry
alpha(delta ')-Michael Addition of Alkyl Amines to Dimethyl (E)-hex-2-en-4-ynedioate: Synthesis of alpha,beta-Dehydroamino Acid Derivatives
(2013-03-01)
Chavan, Arjun S.
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Deng, Jie-Cheng
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Chuang, Shih-Ching
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應用化學系
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Department of Applied Chemistry
The direct nucleophilic addition of alkyl amines to the alpha(delta')-carbon atom of dimethyl (E)-hex-2-en-4-ynedioate to generate alpha,beta-dehydroamino acid derivatives is reported. Herein, we have studied the reactivity of various primary and secondary alkyl amines in the alpha-selective nucleophilic conjugate addition to conjugated dimethyl (E)-hex-2-en-4-ynedioate. The reaction with primary alkyl amines gives only the (2E,4E)-stereoisomer, while that with secondary alkyl amines gives the (2E,4E) and (2Z,4E)-stereoisomers of dimethyl (2-alkylamino)-muconic ester.
Annulation of Benzamides with [60]Fullerene through Palladium(II)-Catalyzed C-H Bond Activation
(2011-03-18)
Chuang, Shih-Ching
;
Rajeshkumar, Venkatachalam
;
Cheng, Chun-An
;
Deng, Jie-Cheng
;
Wang, Guan-Wu
Palladium-catalyzed heteroannulation of N-substituted benzamides with [60]fullerene, which proceeds through direct sp(2) C-H bond activation to form 7-membered ring pallada-intermediate with C(60), led to formation of [60]fulleroisoquinolinones in moderate to good yields (8-64% based on recovered C(60)). A plausible reaction pathway is proposed.
Assembly of Dimethyl Acetylenedicarboxylate and Phosphanes with Aldehydes Leading to gamma-Lactones Bearing alpha-Phosphorus Ylides as Wittig Reagents
(2012-10-01)
Deng, Jie-Cheng
;
Chan, Fu-Wei
;
Kuo, Chih-Wei
;
Cheng, Chun-An
;
Huang, Chien-Yu
We report herein a convenient route to the synthesis of aryl-substituted ?-lactones bearing an a-phosphorus ylide moiety through the assembly of dimethyl acetylenedicarboxylate (DMAD), electron-deficient aldehydes, and triaryl- or trialkylphosphanes in moderate to good yields. The formation of ?-lactones is highly dependent on the reaction time, the phosphane nucleophile, and the molar ratio of DMAD, aldehyde, and phosphane. We found that reactions with a DMAD/aldehyde/tri-p-tolylphosphane molar ratio of 3:1:6 and more electron-deficient aldehydes, such as 4-nitrobenzaldehyde and 4-chloro-3-nitrobenzaldehyde, gave good yields. The isolated ylides reacted with aldehydes as Wittig reagents to give olefins in moderate yields.
Isatin derivatives and isoxazolinones from tandem anti-Michael three-component assembly and oxidation
(2014-08-10)
Deng, Jie-Cheng
;
Chuang, Shih-Ching
;
交大名義發表
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National Chiao Tung University
Multicomponent Reactions of Phosphines, Diynedioates, and Aryl Aldehydes Generated Furans Appending Reactive Phosphorus Ylides through Cumulated Trienoates as Key Intermediates: A Phosphine alpha-Addition-delta-Evolvement of an Anion Pathway
(2014-11-07)
Deng, Jie-Cheng
;
Chuang, Shih-Ching
;
應用化學系
;
Department of Applied Chemistry
Multicomponent reactions of phosphines, diynedioates, and aryl aldehydes have been demonstrated, providing trisubstituted furans appending reactive phosphorus ylides, through cumulated trienoates as key intermediates. The proposed trienoate intermediates, 1,5-dipolar species formed via nucleophilic alpha-attack of phosphines toward diynedioates (alpha-addition-delta-evolvement of an anion, abbreviated alpha A delta E), undergo addition to aryl aldehydes followed by 5-endo-dig cyclization, proton transfer, and resonance to give trisubstituted furans. Furthermore, the phosphorus ylides are oxidized to alpha-keto ester furans and utilized as Wittig reagents.
Multicomponent reactions of phosphines, enynedioates and benzylidene malononitriles generated highly substituted cyclopentenes through an unexpected phosphine alpha-addition-delta-evolvement of an anion pathway
(2016)
Chuang, Shih-Ching
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Sung, Shih-Ping
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Deng, Jie-Cheng
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Chiou, Mong-Feng
;
Hsu, Day-Shin
Multicomponent reactions of phosphines, enynedioates and benzylidene malononitriles provide highly substituted syn-selective cyclopentenes appending the phosphorus ylide moiety in good yield with a diastereoselectivity of up to 100% through resonance-derived 1,5-dipolar species as the key intermediates, via the nucleophilic alpha(delta\')-attack of phosphines toward enynedioates followed by addition to benzylidene malononitriles and 5-exo-dig cyclization. Through computational analyses, the overall reactions for the formation of syn- and anti-diastereomers are both exothermic with 65.6 and 66.3 kcal mol(-1) at the B3LYP-D3/6-31G(d) level of theory and were found to be kinetically controlled, which favours the formation of syn-diastereomers.
Multicomponent Reactions of Phosphines, Enynedioates and Cinnamaldimines Give gamma-Lactams with a 1,3,5-Hexatriene Moiety for Facile 6 pi Electrocyclization: Access to Oxindoles, Isatins and Isoxazolinones
(2015-05-04)
Deng, Jie-Cheng
;
Chen, Wu-Yin
;
Zhu, Chaoyuan
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Chuang, Shih-Ching
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應用化學系
Multicomponent reactions of phosphines, enynedioates and cinnamaldimines generated 3-phosphorus ylide gamma-lactams having a 1,3,5-hexatriene moiety with low activation energy barrier for 6 pi electrocyclization, through initial formation of 1,3-dipoles from the alpha(delta\')-Michael addition of phosphines to enynedioates. The reactive 1,3-dipoles underwent addition to cinnamaldimines, lactamization, 6 pi electrocyclization and oxidation to give 3-phosphorus ylide oxindoles as platform molecules toward isatins and isoxazolinones. The key step, 6 pi electrocyclization, was further examined by a kinetic and a computational study.
Nucleophilic conjugate 1,3-addition of phosphines to oligoynoates
(2014)
Deng, Jie-Cheng
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Kuo, Chih-Wei
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Chuang, Shih-Ching
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應用化學系
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Department of Applied Chemistry
Herein we have elucidated unusual and unique nucleophilic conjugate 1,3-addition reactions of surveyed oligoynoates toward phosphines through spectroscopic and single crystal X-ray diffraction analyses of three-component reaction products of oligoynoates, phosphines and aldehydes.
One-pot formation of fluorescent gamma-lactams having an alpha-phosphorus ylide moiety through three-component alpha(delta ')-Michael reactions of phosphines with an enyne and N-tosyl aldimines
(2014-01-07)
Lin, Yu-Wei
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Deng, Jie-Cheng
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Hsieh, You-Zung
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Chuang, Shih-Ching
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應用化學系
We demonstrate a straightforward synthesis of gamma-lactams possessing an a-phosphorus Aide moiety from assembly of phosphines, N-tosyl aldimines and an enyne through an initial alpha(delta')-attack of phosphines to an enyne in up to 79% yield. The investigated multicomponent reaction tolerates a variety of triaryl-phosphines and electron-poor aldimines to give gamma-lactams in one pot. One of the lactams, with the tri(p-tol)phosphine and 4-cyanophenyl moiety, exhibits fluorescence emission at 447 nm with a quantum yield of 0.11.
Three-component and alpha-Michael reaction of phosphines with En-ynes and aldehydes: Formation of gamma-lactones featuring alpha-phosphorus ylides
(2011-08-28)
Deng, Jie-Cheng
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Chuang, Shih-Ching
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應用化學系
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Department of Applied Chemistry
Three-Component and Nonclassical Reaction of Phosphines with Enynes and Aldehydes: Formation of gamma-Lactones Featuring alpha-Phosphorus Ylides
(2011-05-06)
Deng, Jie-Cheng
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Chuang, Shih-Ching
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應用化學系
;
Department of Applied Chemistry
Inverted carbenoid species, generated from attack of phosphines at the alpha(delta')-carbon of hex-2-en-4-ynedioic acid dialkyl esters, react with aldehydes to give gamma-lactones possessing an alpha-phosphorus ylide moiety.
Uncover nucleophilic conjugate 1,3-addition of phosphines to polyynoates
(2014-08-10)
Chuang, Shih-Ching
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Deng, Jie-Cheng
;
Kuo, Chih-Wei
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應用化學系
;
Department of Applied Chemistry