Asymmetric Synthesis of Hydroxy Esters with Multiple Stereocenters via a Chiral Phosphoric Acid Catalyzed Kinetic Resolution

Asymmetric Synthesis of Hydroxy Esters with Multiple Stereocenters via a Chiral Phosphoric Acid Catalyzed Kinetic Resolution

The kinetic resolution of hydroxy tert-butyl esters through a Brønsted acid catalyzed lactonization is described. The resulting enantioenriched molecules have cyclic backbones and/or multiple stereocenters. DFT calculations explore how small changes in substrate structure can have a large impact on...

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Veröffentlicht in:Journal of organic chemistry 2015-01, Vol.80 (1), p.133-140
Hauptverfasser: Qabaja, Ghassan, Benavides, Amanda R, Liu, Shubin, Petersen, Kimberly S
Format: Artikel
Sprache:eng
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Zusammenfassung:The kinetic resolution of hydroxy tert-butyl esters through a Brønsted acid catalyzed lactonization is described. The resulting enantioenriched molecules have cyclic backbones and/or multiple stereocenters. DFT calculations explore how small changes in substrate structure can have a large impact on the selectivity of the process.
ISSN:0022-3263
1520-6904
DOI:10.1021/jo5022019