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Volumn , Issue 6, 2009, Pages 905-909

Thieme chemistry journal awardees - Where are they now? Phosphine- and Water-Cocatalyzed [3+2] cycloaddition reactions of 2-methyl-2,3-butadienoate with fumarates: A computational and experimental study

(3) Liang, Yong a Liu, Song a Yu, Zhi Xiang a

a PEKING UNIVERSITY (China)

Author keywords

Density functional calculations; Organocatalysis; Phosphine; Reaction mechanisms; Water

Indexed keywords

2 METHYL 2,3 BUTADIENOATE; CARBON; FUMARIC ACID; PHOSPHINE; UNCLASSIFIED DRUG; WATER;

ARTICLE; CALCULATION; CHEMICAL REACTION; CYCLOADDITION; EXPERIMENTAL STUDY; LABELING INDEX;

EID: 64249161117 PISSN: 09365214 EISSN: 14372096 Source Type: Journal
DOI: 10.1055/s-0028-1088203 Document Type: Article

Times cited : (83)

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- General Procedure for the Ph3P- and H2O- Cocatalyzed [3+2] Reaction To a mixture of the fumarate (1 mmol, Ph 3P (0.5 mmol, and H2O (1 mmol) in toluene (5 mL) was added via syringe under nitrogen methyl 2-methylallenoate (0.5 mmol, After stirring at 90 °C for 12 h, the solvent was removed under reduced pressure, and the residue was purified by flash chromatography on Si02 to yield the product. trans-Trimethyl 3-Methylcyclopent-3-ene-l,2,4- tricarboxylate (3) Colorless oil; Rf= 0.27 (PE-EtOAc, 6:1, 1H NMR (300 MHz, CDC13, δ, 2.13 (m, 3 H, 2.90 (ddm, J, 16.5, 6.6 Hz, 1 H, 3.08 (ddm, J, 16.5, 9.6 Hz, 1 H, 3.50 (dt, J, 9.6, 6.6 Hz, 1 H, 3.72 (s, 3 H, 3.74 (s, 3 H, 3.77 (s, 3 H, 3.96 (dm, J, 6.6 Hz, 1 H, 13C NMR 75.5 MHz, CDC13, δ, 14.8, 36.0, 43.4, 51.3, 52.3, 52.4, 59.1, 128.2, 149.7, 165.3, 172.3, 174.0
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