A highly stereoselective transformation of carboxylic esters to trisubstituted olefins via cationic cyclopropyl-allyl rearrangement of sulfonates of cis-1,2-disubstituted cyclopropanols

Tetrahedron Letters

Volumn 48, Issue 48, 2007, Pages 8424-8429

  Kananovich, Dzmitry G ^a   Hurski, Alaksiej L ^a   Kulinkovich, Oleg G ^a  

^a BELARUSIAN STATE UNIVERSITY   (Belarus)

Author keywords

Allyl bromides; Cyclopropanols; Cyclopropyl allyl rearrangement; Stereoselectivity; Titanacyclopropanes; Trisubstituted olefins

Indexed keywords

ALKANOL; ALKENE DERIVATIVE; CYCLOPROPANE DERIVATIVE; CYCLOPROPANOL; ESTER; ETHER; HYDROGEN; MESYLIC ACID; PHOSPHORUS; SULFUR; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL BINDING; CHEMICAL REACTION; CHEMICAL STRUCTURE; CHROMATOGRAPHY; ISOMERISM; STEREOCHEMISTRY;

EID: 35548987440     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2007.09.172     Document Type: Article

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33. No further change in the composition of the product mixture was observed after longer reaction times.
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48. 4. The residue, after the solvent evaporation, was dissolved in DMF (1 mL) and treated with potassium acetate (0.030 g, 0.31 mmol) in the presence of TEBA (0.002 g, 0.01 mmol) at 80 °C for 2 h. After work-up compound 9d (0.075 g, 70%) was isolated by column chromatography (eluent petroleum ether).
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