Palladium-catalyzed [3+2] intramolecular cycloaddition of alk-5-ynylidenecyclopropanes: A rapid, practical approach to bicyclo[3.3.0]octenes

Journal of the American Chemical Society

Volumn 125, Issue 31, 2003, Pages 9282-9283

  Delgado, Alejandro ^a   Rodríguez, J Ramón ^a   Castedo, Luis ^a   Mascareñas, José L ^a  

^a UNIVERSITY OF SANTIAGO DE COMPOSTELA   (Spain)

Author keywords

[No Author keywords available]

Indexed keywords

BICYCLO[3.3.0]OCTANE DERIVATIVE; CYCLOPROPANE DERIVATIVE; PALLADIUM;

ARTICLE; CATALYSIS; CHEMICAL REACTION; CHEMICAL STRUCTURE; CYCLOADDITION; OXIDATION; REACTION ANALYSIS;

BICYCLO COMPOUNDS; CATALYSIS; CYCLIZATION; CYCLOPROPANES; OCTANES; PALLADIUM;

EID: 0043210690     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja0356333     Document Type: Article

References (21)

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18. This compound was prepared by base-promoted coupling of the diethylester of 2-(2-cyclopropylideneethyl)malonic acid to a protected derivative of 4-tosyloxy-but-2-yn-ol (see Supporting Information).
19. Because the chromatographic Rfs of 3a and 4a are very similar, the yield was estimated by integration of NMR signals of the mixture.
20. 3CN led to much lower yields.
21. The alkynyl ester 3f disappears rather rapidly even when the reaction is carried out at 50 °C, leading to products other than the expected cycloadduct, albeit they could not yet be identified.