Palladium-catalyzed [4 + 3] intramolecular cycloaddition of alkylidenecyclopropanes and dienes

Journal of the American Chemical Society

Volumn 129, Issue 36, 2007, Pages 11026-11027

  Gulías, Moisés ^a   Durán, Juan ^a   López, Fernando ^a   Castedo, Luis ^a   Mascareñas, Jose L ^a  

^a UNIVERSITY OF SANTIAGO DE COMPOSTELA   (Spain)

Author keywords

[No Author keywords available]

Indexed keywords

ALKADIENE; ALKYLIDENECYCLOPROPANE DERIVATIVE; DIOXANE; PALLADIUM; PROPANE; TRANSITION ELEMENT; UNCLASSIFIED DRUG;

ARTICLE; CATALYSIS; CHEMICAL STRUCTURE; CYCLOADDITION; ENANTIOSELECTIVITY; ISOMER; ONE POT SYNTHESIS;

EID: 34548711324     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja0756467     Document Type: Article

References (20)

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11. For the synthesis of the precursors, see the Supporting Information.
12. The reaction can be carried out with 4% of the Pd source and 13% of ligand with similar efficiencies, but use of lower loadings leads to a slower reaction and poorer conversions.
13. The enantiomeric excess was determined by HPLC, on the α,β-unsaturated ester isomer (see the Supporting Information).
14. The assignment of the structure and stereochemistry of the cycloadducts is discussed in the Supporting Information.
15. An alternative stepwise process involving zwitterionic intermediates similar to those proposed for the reactions from the Pd-TMM complexes (see ref 4) is less consistent with the observed stereospecificity.
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