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ChemInform Abstract: Effect of Calcium Reagents on Aldol Reactions of Phenolic Enolates with Aldehydes in Alcohol.

✍ Scribed by H. SAIMOTO; K. YOSHIDA; T. MURAKAMI; M. MORIMOTO; H. SASHIWA; Y. SHIGEMASA

Publisher: John Wiley and Sons
Year: 2010
Weight: 34 KB
Volume: 28
Category: Article
ISSN: 0931-7597
DOI: 10.1002/chin.199706082

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✦ Synopsis

Effect of Calcium Reagents on Aldol Reactions of Phenolic Enolates with Aldehydes in Alcohol.

-The aldol-type reaction of phenolic enolates derived from (I) and its analogues with not only water-soluble aldehydes but also hydrophobic aldehydes in MeOH is achieved using divalent metal reagents such as CaCl2/KOH and Ca(OH)2. Their effectiveness is attributed to their ability as Lewis acids to activate the carbonyl group of the aldehyde.

Methyl benzoates with only one hydroxyl group in o-or p-position do not produce any addition products. Aliphatic aldehydes react slowly; the unsaturated aldehyde citral (VIII) forms an intermediate (IX) which cyclizes to the benzopyran (X). This sequence is successfully applied to the one-pot synthesis of racemic cannabichromevarinic acid ( XIII). -(SAIMOTO, H.; YOSHIDA,

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