The Friedel−Crafts-type reaction between properly functionalized inden-1-ones and 2-naphthols generates a hindered single bond which displays a unique preference for an antiperiplanar conformational diastereoisomer. The steric hindrance and the presence of an enantioenriched stereogenic center control the distribution of the two diastereomeric conformers at equilibrium and increase the energy for the rotation of the C(sp3)−C(sp2) single bond.
Nicola Di Iorio, ., Giacomo, F., Andrea, M., Paolo, R., Giorgio, B. (2017). Controlling the C(sp3)−C(sp2) Axial Conformation in the Enantioselective Friedel−Crafts-Type Alkylation of β‑Naphthols with Inden-1-ones. ORGANIC LETTERS, 19, 6692-6695 [10.1021/acs.orglett.7b03415].
Controlling the C(sp3)−C(sp2) Axial Conformation in the Enantioselective Friedel−Crafts-Type Alkylation of β‑Naphthols with Inden-1-ones
Nicola Di Iorio;Andrea Mazzanti;Paolo Righi;Giorgio Bencivenni
2017
Abstract
The Friedel−Crafts-type reaction between properly functionalized inden-1-ones and 2-naphthols generates a hindered single bond which displays a unique preference for an antiperiplanar conformational diastereoisomer. The steric hindrance and the presence of an enantioenriched stereogenic center control the distribution of the two diastereomeric conformers at equilibrium and increase the energy for the rotation of the C(sp3)−C(sp2) single bond.I documenti in IRIS sono protetti da copyright e tutti i diritti sono riservati, salvo diversa indicazione.
