Issue 65, 2014

Synthesis of enantiomerically pure Tröger's base derivatives via chiral disulfoxides

Abstract

The preparation, full characterization and determination of the absolute configuration of diastereomerically pure disulfoxide derivatives of Tröger's base are described. A sulfinyl-lithium exchange followed by the reaction with electrophiles affords synthetically meaningful amounts of enantiomerically pure 4,10-disubstituted Tröger's base analogues without any erosion of the stereogenic information at the nitrogen centers.

Graphical abstract: Synthesis of enantiomerically pure Tröger's base derivatives via chiral disulfoxides

Supplementary files

Article information

Article type
Communication
Submitted
23 May 2014
Accepted
24 Jun 2014
First published
27 Jun 2014

Chem. Commun., 2014,50, 9168-9171

Synthesis of enantiomerically pure Tröger's base derivatives via chiral disulfoxides

P. Ondrisek, R. Schwenk and J. Cvengroš, Chem. Commun., 2014, 50, 9168 DOI: 10.1039/C4CC03963G

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