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Asymmetric Synthesis of Natural Product Inspired Tricyclic Benzopyrones by an Organocatalyzed Annulation Reaction
Author(s) -
Waldmann Herbert,
Khedkar Vivek,
Dückert Heiko,
Schürmann Markus,
Oppel Iris M.,
Kumar Kamal
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.200802413
Subject(s) - annulation , acetylene , natural product , tricyclic , chemistry , yield (engineering) , combinatorial chemistry , organic chemistry , catalysis , materials science , metallurgy
Going back to nature : Electron‐deficient oxadienes and electron‐poor acetylene carboxylates react in the presence of an organocatalyst to give natural product inspired tricyclic benzopyrones efficiently (up to 99 % yield) and stereoselectively (up to 87 % ee ; see scheme). This efficient and operationally simple asymmetric annulation involves the generation of zwitterions from acetylene carboxylates.