A highly stereoselective route to densely functionalized cyclohexanes is described, via a Cinchona-based bifunctional organocatalyzed Henry/Michael/retro-Henry/Henry domino reaction. The peculiar stereoconvergent mechanism allows the creation of up to four contiguous stereocenters in a highly stereodefined manner starting from both achiral aldehydes and racemic nitro alcohols. The simple and efficient protocol can be exploited to synthesize a wide range of substrates and also useful bioactive molecules.
A New Henry/Michael/Retro-Henry/Henry Domino Sequence Promoted by Bifunctional Organocatalysts
QUINTAVALLA, ARIANNA;LOMBARDO, MARCO;TROMBINI, CLAUDIO
2013
Abstract
A highly stereoselective route to densely functionalized cyclohexanes is described, via a Cinchona-based bifunctional organocatalyzed Henry/Michael/retro-Henry/Henry domino reaction. The peculiar stereoconvergent mechanism allows the creation of up to four contiguous stereocenters in a highly stereodefined manner starting from both achiral aldehydes and racemic nitro alcohols. The simple and efficient protocol can be exploited to synthesize a wide range of substrates and also useful bioactive molecules.File in questo prodotto:
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