Organocatalytic Stereoselective Iodoamination of Alkenes

Organocatalytic Stereoselective Iodoamination of Alkenes

A new chiral thiohydantoin catalyst is used for the stereoselective iodoamination of alkenes. N‐iodosuccinimide as the source of the electrophilic iodine is activated by catalytic amounts of different additives which also influence the regioselectivity of some cyclizations. An unexplored class of ch...

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Veröffentlicht in:Chemistry : a European journal 2014-10, Vol.20 (41), p.13113-13116
Hauptverfasser: Mizar, Pushpak, Burrelli, Alessandra, Günther, Erika, Söftje, Martin, Farooq, Umar, Wirth, Thomas
Format: Artikel
Sprache:eng
Schlagworte:
Activated
Additives
Alkenes
Catalysis
Catalysts
Chemistry
cyclization
diamination
hypervalent iodine
Iodine
organocatalysis
stereoselective synthesis
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Beschreibung
Zusammenfassung:A new chiral thiohydantoin catalyst is used for the stereoselective iodoamination of alkenes. N‐iodosuccinimide as the source of the electrophilic iodine is activated by catalytic amounts of different additives which also influence the regioselectivity of some cyclizations. An unexplored class of chiral thiohydantoins can be used as efficient catalysts for iodoaminations while additives effect the regiochemistry. Also quaternary stereocenters can be easily generated with this metal‐free, organocatalytic protocol (NIS=N‐iodosuccinimide).
ISSN:0947-6539
1521-3765
DOI:10.1002/chem.201404762