Tertiary Aminourea-Catalyzed Enantioselective Iodolactonization

Tertiary Aminourea-Catalyzed Enantioselective Iodolactonization

Binding the anion: A highly enantioselective iodolactonization of 5‐hexenoic acids has been achieved using a tertiary aminourea‐catalyst (see scheme). The use of catalytic iodine in this process is critical to enhancing both the reactivity and enantioselectivity of the stoichiometric I+ source. The...

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Veröffentlicht in:Angewandte Chemie (International ed.) 2010-09, Vol.49 (40), p.7332-7335
Hauptverfasser: Veitch, Gemma E, Jacobsen, Eric N
Format: Artikel
Sprache:eng
Schlagworte:
Amines - chemistry
anion binding
asymmetric catalysis
Catalysis
halogenation
Iodine - chemistry
iodolactonization
Lactones - chemistry
Molecular Structure
organocatalysis
Stereoisomerism
Urea - chemistry
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Zusammenfassung:Binding the anion: A highly enantioselective iodolactonization of 5‐hexenoic acids has been achieved using a tertiary aminourea‐catalyst (see scheme). The use of catalytic iodine in this process is critical to enhancing both the reactivity and enantioselectivity of the stoichiometric I+ source. The mechanism is proposed to involve binding of an iodonium imidate intermediate by the H‐bond donor catalyst.
ISSN:1433-7851
1521-3773
DOI:10.1002/anie.201003681