Expedient synthesis of bicyclo[3.2.1]octanes and bicyclo[3.3.1]nonanes via the double Michael addition to cyclic dienones†,10.1039/C3RA43923B

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Lactoyl-CoA 全氟丁基戊烷白叶藤碱全氟己基辛烷新白叶藤碱壳寡糖特色专题-生物多肽

Expedient synthesis of bicyclo[3.2.1]octanes and bicyclo[3.3.1]nonanes via the double Michael addition to cyclic dienones†

Aurélie Moulia,Joycelyn Teo,Charles W. Johannes,Jean-Alexandre Richard

RSC Advances Pub Date : 10/15/2013 00:00:00 , DOI:10.1039/C3RA43923B

Abstract

We report the expedient synthesis of 8-disubstituted bicyclo[3.2.1]octane-3-ones and 9-disubstituted bicyclo[3.3.1]octane-3-ones through the double Michael addition (DMA) of carbon nucleophiles to 7 and 8-membered ring dienones. The reaction proceeds in 42–96% yield with an interesting control of the stereochemistry of the bridged secondary, tertiary or quaternary centre.