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Issue 45, 2012

Chiral proton catalysis of secondary nitroalkane additions to azomethine: synthesis of a potent GlyT1 inhibitor

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Abstract

The first enantioselective synthesis of a potent GlyT1 inhibitor is described. A 3-nitroazetidine donor is used in an enantioselective aza-Henry reaction catalyzed by a bis(amidine)-triflic acid salt organocatalyst, delivering the key intermediate with 92% ee. This adduct is reductively denitrated and converted to the target through a short sequence, thereby allowing assignment of the absolute configuration of the more potent enantiomer.

Graphical abstract: Chiral proton catalysis of secondary nitroalkane additions to azomethine: synthesis of a potent GlyT1 inhibitor

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Article information


Submitted
27 Mar 2012
Accepted
05 Apr 2012
First published
30 Apr 2012

Chem. Commun., 2012,48, 5578-5580
Article type
Communication

Chiral proton catalysis of secondary nitroalkane additions to azomethine: synthesis of a potent GlyT1 inhibitor

T. A. Davis, M. W. Danneman and J. N. Johnston, Chem. Commun., 2012, 48, 5578 DOI: 10.1039/C2CC32225K

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