Asymmetric Catalytic Aza‐Diels–Alder/Ring‐Closing Cascade Reaction Forming Bicyclic Azaheterocycles by Trienamine Catalysis | Zendy

Li Yang | Zendy; Barløse Casper | Zendy; Jørgensen Julie | Zendy; Carlsen Bjørn Dreiø | Zendy; Jørgensen Karl Anker | Zendy

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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.

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