Asymmetric Synthesis of 2,3-Dihydrobenzofurans by a [4+1] Annulation Between Ammonium Ylides and In Situ Generated o-Quinone Methides.
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.
Johannes Kepler University Linz, Institute of Organic Chemistry, Altenbergerstrasse 69, 4040, Linz, Austria.
Nicole
N
Meisinger
Johannes Kepler University Linz, Institute of Organic Chemistry, Altenbergerstrasse 69, 4040, Linz, Austria.
Lukas
L
Roiser
Johannes Kepler University Linz, Institute of Inorganic Chemistry, Altenbergerstrasse 69, 4040, Linz, Austria.
Uwe
U
Monkowius
Johannes Kepler University Linz, Institute of Analytical Chemistry, Altenbergerstrasse 69, 4040, Linz, Austria.
Markus
M
Himmelsbach
Université catholique de Louvain, Institute of Condensed Matter and Nanosciences, Place Louis Pasteur 1 box L4.01.02, 1348, Louvain-la-Neuve, Belgium.
Raphaël
R
Robiette
Johannes Kepler University Linz, Institute of Organic Chemistry, Altenbergerstrasse 69, 4040, Linz, Austria.
Mario
http://orcid.org/0000-0002-8421-8642
M
Waser
annulation; asymmetric synthesis; chiral auxiliaries; density functional calculations; quinone methides; ylides