Direct generation of lithium homoenolates from 3-aryl α,β-unsaturated ketones or esters by an arene-catalysed lithiation: Synthesis of substituted tetrahydrofurans and γ-butyrolactones

Tetrahedron

Volumn 53, Issue 7, 1997, Pages 2641-2652

  Alonso, Emma ^a   Ramón, Diego J ^a   Yus, Miguel ^a  

^a UNIVERSITY OF ALICANTE   (Spain)

Author keywords

[No Author keywords available]

Indexed keywords

LACTONE DERIVATIVE; TETRAHYDROFURAN DERIVATIVE;

ARTICLE; CHIRALITY; DRUG SYNTHESIS; IN VITRO STUDY; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; PRIORITY JOURNAL; REACTION ANALYSIS; STEREOCHEMISTRY;

EID: 0031575589     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4020(96)01155-6     Document Type: Article

References (35)

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23. 15. In spite of the "normal" reactivity of carbonyl compounds with diamagnetic nucleophiles, a possible attack of a radical anion of the type VII to the carbonyl compound can not be ruled out. For a related mechanism involving ethyl β-arylacrylates, aldehydes and magnesium, see: Ohno, T.; Ishino, Y.; Tsumagari, Y.; Nishiguchi, I. J. Org. Chem. 1995, 60, 458-460. Since in our case the reaction works also with ketones we think that a dianion of the type VIII is the most probable species involved in the nucleophilic attack to the carbonyl compound. We thank the referee for suggesting us the mentioned radical alternative.
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