ChemInform Abstract: AlCl₃‐Mediated Direct Carbon—Carbon Bond‐Forming Reaction of α‐Hydroxyketene‐S,S‐acetals with Arenes and Synthesis of 3,4‐Disubstituted Dihydrocoumarin Derivatives.

Abstract

2008 C-C bond formation O 0282AlCl3-Mediated Direct Carbon-Carbon Bond-Forming Reaction of α-Hydroxyketene-S,S-acetals with Arenes and Synthesis of 3,4-Disubstituted Dihydrocoumarin Derivatives. -In the presence of AlCl3 α-hydroxyketeneacetals efficiently react with arenes to afford products of type (III) and (VI). Coupling of the acyclic acetals (VII), (XI), and (XIV) with phenols and naphthols allows facile access to 3,4-substituted dihydrocoumarins and chromene derivatives. -(PIAO, C.-R.; ZHAO*, Y.-L.; HAN, X.-D.; LIU, Q.; J.

Brønsted-Acid-Catalyzed Synthesis of 3-Alkoxy and 3-Sulfamido Indanones via a Tandem Cyclization

“…23 Then, the intramolecular α-acylvinyl addition of B with the formyl group furnishes the 3-hydroxy indanone intermediate C, accompanied by proton migration. 24 Later, in the presence of protonic acid, the hydroxyl of C gets activated, generating the allylic carbonium ion D. 25 Finally, D is attacked by nucleophilic alcohols or sulfamides by S N 1 reaction to obtain the desired 3-alkoxy and sulfamido indanones.…”