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Transannular cyclization with Grignard reagents: an efficient synthesis of oxaadamantane and protoadamantane derivatives

Grignard reagents are among the most useful organometallic in organic synthesis. Besides the classical nucleophilicreactions to the carbonyl compounds, they become useful in synthetic organic chemistry and gain versatile reactivity, especially whencombined with different metal salts. Herein we report facile and efficient preparation of novel oxaadamantane derivative and as well as the protoadamantane derivatives. Reaction of 7-exo-epoxymethylenebicyclo[3.3.1]nonan-3-one with the corresponding Grignard reagents afforded a mixture of protoadamantane stereoisomers. However, when Ce-salt was added the corresponding oxaadamantane species was isolated as a sole product. Stereochemistry and the mechanistic aspects of these reactiuons will be discussed.

Oxoadamantane derivatives; Protoadamantane derivatives; Grignard reagents

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