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An Enantioselective Inverse‐Electron‐Demand Imino Diels–Alder Reaction
Author(s) -
EschenbrennerLux Vincent,
Küchler Philipp,
Ziegler Slava,
Kumar Kamal,
Waldmann Herbert
Publication year - 2014
Publication title -
angewandte chemie
Language(s) - English
Resource type - Journals
eISSN - 1521-3757
pISSN - 0044-8249
DOI - 10.1002/ange.201309022
Subject(s) - enantioselective synthesis , chromone , chemistry , diels–alder reaction , catalysis , ring (chemistry) , combinatorial chemistry , organic chemistry
The imino Diels–Alder reaction is an efficient method for the synthesis of aza‐heterocycles. While different stereo‐ and enantioselective inverse‐electron‐demand imino Diels–Alder (IEDIDA) reactions have been reported before, IEDIDA reactions including electron‐deficient dienes are unprecedented. The first enantioselective IEDIDA reaction between electron‐poor chromone dienes and cyclic imines, catalyzed by zinc/binol complexes is described. The novel reaction provides a facile entry to a natural product inspired collection of ring‐fused quinolizines including a potent modulator of mitosis.