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Issue 64, 2017
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Catalytic enantioselective aza-Diels–Alder reactions of unactivated acyclic 1,3-dienes with aryl-, alkenyl-, and alkyl-substituted imines

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Abstract

A catalytic enantioselective aza-Diels–Alder reaction of unactivated acyclic dienes with aryl-, alkenyl-, and alkyl-substituted imines is described. With 5–10 mol% loadings of a new Brønsted acid catalyst, the aza-Diels–Alder reaction of unactivated acyclic dienes proceeded to give the corresponding aza-Diels–Alder adducts in high yields (up to 98%) with excellent enantioselectivity (up to 98% ee). Preliminary DFT calculations suggest that the reaction proceeds through a chiral ion pair intermediate.

Graphical abstract: Catalytic enantioselective aza-Diels–Alder reactions of unactivated acyclic 1,3-dienes with aryl-, alkenyl-, and alkyl-substituted imines

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Publication details

The article was received on 19 Apr 2017, accepted on 19 Jul 2017 and first published on 19 Jul 2017


Article type: Communication
DOI: 10.1039/C7CC03010J
Citation: Chem. Commun., 2017,53, 8996-8999

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    Catalytic enantioselective aza-Diels–Alder reactions of unactivated acyclic 1,3-dienes with aryl-, alkenyl-, and alkyl-substituted imines

    Y. Hatanaka, S. Nantaku, Y. Nishimura, T. Otsuka and T. Sekikaw, Chem. Commun., 2017, 53, 8996
    DOI: 10.1039/C7CC03010J

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