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Carbamoyl Translocations by an Anionic ortho ‐Fries and Cumulenolate α‐Acylation Pathway: Regioselective Synthesis of Polysubstituted Chromone 3‐ and 8‐Carboxamides
Author(s) -
Macklin Todd K.,
Panteleev Jane,
Snieckus Victor
Publication year - 2008
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.200704360
Subject(s) - regioselectivity , chromone , fries rearrangement , chemistry , borylation , acylation , metalation , iridium , aryl , stereochemistry , catalysis , combinatorial chemistry , organic chemistry , alkyl
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 B 2 pin 2 borylation lead to the construction of polysubstituted chromones, which are key components of many bioactive compounds.