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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 , in situ , ammonium , quinone , chemistry , organic chemistry , medicinal chemistry , catalysis
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.