Amine‐Urea‐Mediated Asymmetric Cycloadditions between Nitrile Oxides and  o ‐Hydroxystyrenes by Dual Activation | Zendy

Suga Hiroyuki | Zendy; Hashimoto Yohei | Zendy; Toda Yasunori | Zendy; Fukushima Kazuaki | Zendy; Esaki Hiroyoshi | Zendy; Kikuchi Ayaka | Zendy

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Amine‐Urea‐Mediated Asymmetric Cycloadditions between Nitrile Oxides and o ‐Hydroxystyrenes by Dual Activation

Author(s) -

Suga Hiroyuki,

Hashimoto Yohei,

Toda Yasunori,

Fukushima Kazuaki,

Esaki Hiroyoshi,

Kikuchi Ayaka

Publication year - 2017

Publication title -

angewandte chemie

Language(s) - English

Resource type - Journals

eISSN - 1521-3757

pISSN - 0044-8249

DOI - 10.1002/ange.201705662

Subject(s) - nitrile , chemistry , enantioselective synthesis , bifunctional , amine gas treating , cinchona , brønsted–lowry acid–base theory , catalysis , cycloaddition , homo/lumo , hydrogen bond , organic chemistry , combinatorial chemistry , photochemistry , molecule

The first example of asymmetric 1,3‐dipolar cycloadditions between nitrile oxides and o ‐hydroxystyrenes, mediated by cinchona‐alkaloid‐based amine‐ureas is reported. The method is based on a dual activation involving both LUMO and HOMO activations. In addition to the stoichiometric asymmetric induction, a catalytic amount of amine‐urea enables the cycloadditions to proceed in an enantioselective manner. Computational studies strongly support the HOMO activation of o ‐hydroxystyrenes and LUMO activation of nitrile oxides by hydrogen‐bonding interactions with the Brønsted acid/base bifunctional catalyst.

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