An enantioselective inverse-electron-demand imino Diels-Alder reaction.
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.
Max-Planck- Institut für molekulare Physiologie, Otto-Hahn-Strasse 11, 44227 Dortmund (Germany); Technische Universität Dortmund, Fachbereich Chemie und Chemische Biologie, 44221 Dortmund (Germany).
Vincent
V
Eschenbrenner-Lux
Philipp
P
Küchler
Slava
S
Ziegler
Kamal
K
Kumar
Herbert
H
Waldmann
D020090:Chromosome Segregation / Q000187:drug effects; D056831:Coordination Complexes / Q000737:chemistry; D061565:Cycloaddition Reaction; D004583:Electrons; D006367:HeLa Cells; D006801:Humans; D007097:Imines / Q000138:chemical synthesis / Q000737:chemistry* / Q000494:pharmacology; D018613:Microscopy, Confocal; D008938:Mitosis / Q000187:drug effects; D011807:Quinolizines / Q000737:chemistry; D013237:Stereoisomerism; D015032:Zinc / Q000737:chemistry
D056831:Coordination Complexes; D007097:Imines; D011807:Quinolizines; D015032:Zinc
asymmetric catalysis; cycloadditions; heterocycles; natural products; zinc