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Issue 12, 2012
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Furanyl cyclic amines: a diastereoselective synthesis of 2,6-syn-disubstituted piperidines under thermodynamic control

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Abstract

Utilising the propensity of the 2-furanyl group to facilitate equilibration of an adjacent tosylamide chiral centre, a diastereoselective route to 2,6-syn-piperidines was developed that proceeds with high levels of thermodynamic stereocontrol. X-ray crystallography structures suggest that, as seen in similar systems, pseudo-allylic strain between the N-tosyl group and the substituents at the 2 and 6 positions dominates stereochemical preference, overriding 1,3 diaxial interactions.

Graphical abstract: Furanyl cyclic amines: a diastereoselective synthesis of 2,6-syn-disubstituted piperidines under thermodynamic control

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Publication details

The article was received on 29 Nov 2011, accepted on 06 Jan 2012 and first published on 09 Jan 2012


Article type: Communication
DOI: 10.1039/C2OB07008A
Citation: Org. Biomol. Chem., 2012,10, 2392-2394
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    Furanyl cyclic amines: a diastereoselective synthesis of 2,6-syn-disubstituted piperidines under thermodynamic control

    M. O'Brien, A. Leach, R. J. Armstrong, K. Chong and R. Sheridan, Org. Biomol. Chem., 2012, 10, 2392
    DOI: 10.1039/C2OB07008A

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