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Asymmetric Catalytic Aza‐Diels–Alder/Ring‐Closing Cascade Reaction Forming Bicyclic Azaheterocycles by Trienamine Catalysis
Author(s) -
Li Yang,
Barløse Casper,
Jørgensen Julie,
Carlsen Bjørn Dreiø,
Jørgensen Karl Anker
Publication year - 2017
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201604310
Subject(s) - bicyclic molecule , cycloaddition , catalysis , chemistry , ring (chemistry) , diels–alder reaction , cascade reaction , yield (engineering) , stereochemistry , combinatorial chemistry , medicinal chemistry , organic chemistry , physics , thermodynamics
An asymmetric catalytic aza‐Diels–Alder/ring‐closing cascade reaction between acylhydrazones and in situ formed trienamines is presented. The reaction proceeds through a formal aza‐Diels–Alder cycloaddition, followed by a ring‐closing reaction forming the hemiaminal ring leading to chiral bicyclic azaheterocycles in moderate to good yield (up to 71 %), good enantio‐ (up to 92 % ee ) and diastereoselectivity (up to >20:1 d.r.). Furthermore, transformations are presented to show the potential application of the formed product.