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(sp(3))-C(sp(2)) single bond.

Controlling the C(sp3)-C(sp2) Axial Conformation in the Enantioselective Friedel-Crafts-Type Alkylation of β-Naphthols with Inden-1-ones

Filippini, Giacomo;
2017-01-01

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(sp(3))-C(sp(2)) single bond.
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Utilizza questo identificativo per citare o creare un link a questo documento: https://hdl.handle.net/11368/3030862
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