Organic Letters
Organic Letters
5 years ago

Asymmetric Synthesis of Functionalized Tricyclic Chromanes via an Organocatalytic Triple Domino Reaction

Asymmetric Synthesis of Functionalized Tricyclic Chromanes via an Organocatalytic Triple Domino Reaction
Kari Rissanen, Mukesh Kumar, Pankaj Chauhan, Arto Valkonen, Dieter Enders
A highly stereoselective triple domino reaction for the synthesis of functionalized tricyclic chromane scaffolds has been developed. A secondary amine-catalyzed domino Michael/Michael/aldol condensation reaction between aliphatic aldehydes, nitro-chromenes, and α,β-unsaturated aldehydes leads to the formation of synthetically important tricyclic chromanes bearing four contiguous stereogenic centers including a tetrasubstituted carbon in good yields (20–66%) and excellent stereoselectivities (>20:1 dr and >99% ee).

Publisher URL: http://dx.doi.org/10.1021/acs.orglett.7b01322

DOI: 10.1021/acs.orglett.7b01322

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