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Tertiary Aminourea‐Catalyzed Enantioselective Iodolactonization
Author(s) -
Veitch Gemma E.,
Jacobsen Eric N.
Publication year - 2010
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.201003681
Subject(s) - enantioselective synthesis , catalysis , reactivity (psychology) , chemistry , combinatorial chemistry , organic chemistry , computer science , pathology , medicine , alternative medicine
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.