Beilstein J. Org. Chem.2021,17, 2642–2649, doi:10.3762/bjoc.17.177
-unsaturated carbonyl compounds catalyzed by bifunctional squaramide catalysts has been developed. This methodology offers both enantiomers of β-silylnitroalkanes in good to excellent yields (up to 92%) and enantioselectivities (up to 97.5% ee) under solvent-free conditions at room temperature. Control
experiments reveal that the presence of a β-silyl group in the enones is crucial for high reactivity under the optimized reaction conditions.
Keywords: β-silyl α,β-unsaturated carbonyl compounds; β-silylnitroalkanes; chiral organosilanes; organocatalysis; solvent-free synthesis; Introduction
organosilanes [29][37][38], we present herein an organocatalyzed conjugate addition reaction of nitromethane to β-silyl enones to afford chiral β-silylnitroalkanes (Scheme 1). Notably, the developed method was not only carried out under solvent-free conditions at room temperature but was found to be tolerant
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Graphical Abstract
Scheme 1:
Selected methods for the synthesis of enantioenriched β-silyl nitroalkanes, synthesis of chiral org...