Organocatalytic Michael Addition of Unactivated α-Branched Nitroalkanes to Afford Optically Active Tertiary
Beñat Lorea1, Ane García-Urricelqui2, José M Odriozola1
1Departamento de Ciencias, Institute for Advanced Materials and Mathematics (InaMat2), Universidad Pública de Navarra (UPNA), 31006 Pamplona, Spain.
Abstract:
The direct, asymmetric conjugate addition of unactivated α-branched nitroalkanes is developed based on the combined use of chiral amine/ureidoaminal bifunctional catalysts and a tunable acrylate template to provide tertiary nitrocompounds in 55-80% isolated yields and high enantioselectivity (e.r. up to 96:4). Elaboration of the ketol moiety in thus obtained adducts allows a fast entry to not only carboxylic and aldehyde derivatives but also nitrile compounds and enantioenriched 5,5-disubstituted γ-lactams.
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