A general approach for the asymmetric synthesis of densely substituted piperidines and fully substituted piperidinones employing the asymmetric Mannich reaction as key step?

RSC Advances Pub Date: 2013-10-01 DOI: 10.1039/C3RA45110K

Abstract

Two efficient and alternative protocols for the preparation of highly enantioenriched piperidine structures are reported. We have also developed a simple route to access to fully diastereo- and enantioenriched substituted piperidinones. The key step of all this synthesis relies on a diastereoselective Mannich reaction, employing the readily available aminoalcohol (+)-(S,S)-pseudoephedrine as a chiral auxiliary, which allows the preparation of β-aminocarbonyl compounds in high yield, diastereo and enantioselectivity and using easy-to-scale protocols.

Graphical abstract: A general approach for the asymmetric synthesis of densely substituted piperidines and fully substituted piperidinones employing the asymmetric Mannich reaction as key step
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