The asymmetric conjugate addition of carbon and heteroatom nucleophiles to nitroalkenes is a very interesting tool for the construction of highly functionalized synthetic building blocks. Thanks to the rapid development of asymmetric organocatalysis, significant progress has been made during the last years in achieving efficiently this process, concerning chiral organocatalysts, substrates and reaction conditions. This review surveys the advances in asymmetric organocatalytic conjugate addition reactions to α,β-unsaturated nitroalkenes developed between 2013 and early 2017.

The Sonogashira cross-coupling reaction is the most frequently employed synthetic procedure for the preparation of arylated alkynes, which are important conjugated compounds with multiple applications. Despite of their rather high price, this reaction is usually catalyzed by palladium species, making the recovery and reuse of the catalyst an interesting topic, mainly for industrial purposes. Easy recycle can be achieved anchoring the palladium catalyst to a separable support. This review shows recent developments in the use of palladium species anchored to different solid supports as recoverable catalysts for Sonogashira cross-coupling reactions.

Primary amine-salicylamides derived from chiral trans-cyclohexane-1,2-diamines are used as organocatalysts for the enantioselective conjugate addition of α,α-disubstituted aldehydes to arylated and heteroarylated nitroalkenes. The reaction is performed in the presence of 4-dimethylaminopyridine as an additive in dichloromethane as a solvent at room temperature. The corresponding enantioenriched γ-nitroaldehydes are obtained with enantioselectivities up to 95%. Theoretical calculations are used to justify the reasons of the stereoinduction.

The DTBB-catalyzed lithiation of bis(chloromethyl) sulfone (1) and sulfoxide (3) in the presence of different carbonyl compounds [t-BuCHO, c-C₆H₁₁CHO, PhCHO, Me₂CO, Et₂CO, n-Pr₂CO, (CH₂)₄CO, (CH₂)₅CO, (c-C₃H₅)₂CO, PhCOMe, norbonan-2-one] in THF at -90 ºC, followed by hydrolysis with water at the same temperature led to the formation of the corresponding dihydroxy sulfones (2) or sulfoxides (4). Representative compounds of both series have been analyzed by X-ray crystallography.