Naturalproductman’s Blog

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Meerwein-Ponndorf-Verley followed by Brooke

Posted by naturalproductman on June 2, 2011

The Meerwein-Ponndorf-Verley reduction is the opposite of the Oppenauer oxidation.  Kei Takeda and co-workers from Hiroshima University have reported in ACIEE on a Meerwein-Ponndorf-Verley type reduction of an acyl silane followed by a Brooke rearrangement to afford siloxyallenes.  They were able to trap these allenes with a dienophile to undergo a [4+2] cycloaddition.

cycloaddition
ACIEE paper

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