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. Quintavalla, M. Lombardo, S. P. Sanap, C. Trombini (2013). A New Henry/Michael/Retro-Henry/Henry Domino Sequence Promoted by Bifunctional Organocatalysts. ADVANCED SYNTHESIS & CATALYSIS, 355, 938-946 [10.1002/adsc.201201135].
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.I documenti in IRIS sono protetti da copyright e tutti i diritti sono riservati, salvo diversa indicazione.
