Organoyttrium-catalyzed sequential cyclization/silylation reactions of nitrogen-heteroaromatic dienes demonstrating 'aryl-directed' regioselectivity

Journal of Organic Chemistry

Volumn 65, Issue 12, 2000, Pages 3767-3770

  Molander, Gary A ^a,b   Schmitt, Monika H ^b  

^a UNIVERSITY OF PENNSYLVANIA   (United States)

^b UNIVERSITY OF COLORADO   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ALKADIENE; AROMATIC COMPOUND; SILANE DERIVATIVE;

ARTICLE; CATALYSIS; CYCLIZATION; MOLECULAR INTERACTION; STEREOCHEMISTRY; UNITED STATES;

EID: 0034674449     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo0000527     Document Type: Article

References (43)

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39. 2O, 3.2 mmol) was added at -78°C, and the reaction was warmed to room temperature. After the solution was stirred for 4 h, the solvent was removed and the solids were extracted with hexanes to provide the desired organometallics.
40. One problem with the catalyst is that it apparently becomes deactivated over time because of hydride dimer formation. Ideal conditions involve the addition of smaller portions of the catalyst at fixed intervals to maintain an active concentration of the catalyst.
41. The general workup procedure involved filtration of the crude mixture through a small plug of Florisil prior to concentration by rotary evaporation and purification by flash chromatography. Many of these reactions are so clean, in fact, that pouring the reaction mixture through a short bed of Florisil to remove the catalyst, followed by evaporation of the solvent and bulb-to-bulb distillation, leads to essentially quantitative yields of analytically pure products.
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43. The relative stereochemistry of the major isomer of 2 was assigned on the basis of NOE difference experiments using alcohol 3.