Carbamoyl Translocations by an Anionic ortho-Fries and Cumulenolate α-Acylation Pathway: Regioselective Synthesis of Polysubstituted Chromone 3- and 8-Carboxamides

Completing the circle: A synthesis of chromone 3‐ and 8‐carboxamides (3 and 4) from 2‐but‐2‐ynoyl aryl O‐carbamates 1 has been achieved via common intermediate 2 in a regioselective manner. Repetitive metalation reactions and an iridium‐catalyzed B2pin2 borylation lead to the construction of polysub...

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Bibliographic Details
Published in:Angewandte Chemie (International ed.) 2008-02, Vol.47 (11), p.2097-2101
Main Authors: Macklin, Todd K, Panteleev, Jane, Snieckus, Victor
Format: Article
Language:English
Subjects:
Acylation
Amides - chemical synthesis
Amides - chemistry
anionic reactions
Anions - chemistry
Carbamates - chemistry
Chromones - chemical synthesis
Chromones - chemistry
heterocycles
metalation
Molecular Structure
organolithium reagents
Stereoisomerism
synthetic methods
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Summary:Completing the circle: A synthesis of chromone 3‐ and 8‐carboxamides (3 and 4) from 2‐but‐2‐ynoyl aryl O‐carbamates 1 has been achieved via common intermediate 2 in a regioselective manner. Repetitive metalation reactions and an iridium‐catalyzed B2pin2 borylation lead to the construction of polysubstituted chromones, which are key components of many bioactive compounds.
ISSN:1433-7851
1521-3773
DOI:10.1002/anie.200704360