Asymmetric Synthesis of 2,3‐Dihydrobenzofurans by a [4+1] Annulation Between Ammonium Ylides and In Situ Generated  o ‐Quinone Methides | Zendy

Meisinger Nicole | Zendy; Roiser Lukas | Zendy; Monkowius Uwe | Zendy; Himmelsbach Markus | Zendy; Robiette Raphaël | Zendy; Waser Mario | Zendy

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Asymmetric Synthesis of 2,3‐Dihydrobenzofurans by a [4+1] Annulation Between Ammonium Ylides and In Situ Generated o ‐Quinone Methides

Author(s) -

Meisinger Nicole,

Roiser Lukas,

Monkowius Uwe,

Himmelsbach Markus,

Robiette Raphaël,

Waser Mario

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.201700171

Subject(s) - annulation , quinone , in situ , chemistry , ammonium , stereoselectivity , reactivity (psychology) , organic chemistry , combinatorial chemistry , stereochemistry , catalysis , medicine , alternative medicine , pathology

A highly enantio‐ and diastereoselective [4+1] annulation between in situ generated ammonium ylides and o ‐quinone methides for the synthesis of a variety of 2,3‐dihydrobenzofurans has been developed. The key factors controlling the reactivity and stereoselectivity were systematically investigated by experimental and computational means and the energy profiles obtained provide a deeper insight into the mechanistic details of this reaction.

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