A domino reaction of tetrahalo- 7,7-dimethoxybicyclo[2.2.1]heptenyl alcohols leading to indenones and a de novo synthesis of ninhydrin derivatives

Kaki, R B and Khan, Faiz Ahmed (2015) A domino reaction of tetrahalo- 7,7-dimethoxybicyclo[2.2.1]heptenyl alcohols leading to indenones and a de novo synthesis of ninhydrin derivatives. Organic and Biomolecular Chemistry (13). pp. 299-308. ISSN 1477-0520

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Abstract

An efficient acid induced rearrangement of a tetrahalo-7,7-dimethoxybicyclo[2.2.1]heptenyl system leading to substituted indenones is reported. This domino reaction involves dehydration, olefin isomerization, ketal hydrolysis, [3,3]-sigmatropic rearrangement and dehydrohalogenation. The resultant vicinal dihalo olefin moiety in the efficiently generated indenone derivatives was utilized to transform into ninhydrin derivatives by employing Ru(III)-catalyzed oxidation.

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