Organocatalytic Michael Addition of Unactivated α-Branched Nitroalkanes to Afford Optically Active Tertiary Nitrocompounds
Date
2023-11-27Author
Lorea, Beñat
García Urricelqui, Ane
Odriozola, José M.
Razkin, Jesús
Espinal Viguri, Maialen
García, Jesús M.
Palomo Nicolau, Claudio
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Organic Letters 25(48) : 8590-8595 (2023)
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.