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

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 enantiome...

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Bibliographic Details
Published in:Chemical communications (Cambridge, England) England), 2014-08, Vol.50 (65), p.9168-9171
Main Authors: Ondrisek, Pavol, Schwenk, Rino, Cvengroš, Ján
Format: Article
Language:English
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Summary: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.
ISSN:1359-7345
1364-548X
DOI:10.1039/c4cc03963g