Efficient methodology for alkylation of vinylnitroso compounds with carbon nucleophiles.

@article{Li2010EfficientMF,
  title={Efficient methodology for alkylation of vinylnitroso compounds with carbon nucleophiles.},
  author={Puhui Li and Max M Majireck and Jason A. Witek and Steven M Weinreb},
  journal={Tetrahedron letters},
  year={2010},
  volume={51 15},
  pages={
          2032-2035
        }
}
20 Citations
Synthesis of α-Substituted Enoximes with Nucleophiles via Nitrosoallenes.
TLDR
Nucleophilic substitution of nitrosoallenes, a novel chemical species prepared from allenyl N-hydroxysulfonamides, afforded α-functionalized enoximes, and introduction of various nucleophiles proceeded smoothly to form C-N,C-O, C-S, c-F, and C-C bonds in the presence of azodicarboxylates.
Michael Addition of P-Nucleophiles to Conjugated Nitrosoalkenes.
TLDR
A general approach to various α-phosphorus-substituted oximes was developed, which can be considered as useful P-, N-, and O-ligands for catalysis and precursors to valuable β-aminophosphonates.
Conjugated nitrosoalkenes as Michael acceptors in carbon–carbon bond forming reactions: a review and perspective
TLDR
The present review deals with carbon–carbon bond forming reactions involving Michael addition to α-nitrosoalkenes with a particular focus on recent developments in this methodology and its use in total synthesis.
Recent Advances in the Chemistry of Conjugated Nitrosoalkenes and Azoalkenes.
This review aims to present the most recent contributions in the chemistry of nitrosoalkenes and azoalkenes, highlighting the chemical behavior that makes them important and versatile building blocks
Convergent approach to the tetracyclic core of the apparicine class of indole alkaloids via a key intermolecular nitrosoalkene conjugate addition.
Readily available methyl 3-formylindol-2-ylacetate and N-tosyl-4-chloro-3-piperidone oxime have been used to construct the tetracyclic skeleton of the apparicine class of monoterpene indole alkaloids
Formal [3+2] Cycloaddition of Nitrosoallenes with Carbonyl and Nitrile Compounds to Form Functional Cyclic Nitrones.
The synthesis of functional cyclic nitrones via [3+2] cycloadditions of allenamide-derived nitrosoallenes with carbonyl/nitrile compounds, including ketones, esters, and nitriles, is presented
A one-pot synthesis of 7-phenylindolo[3,2-a]carbazoles from indoles and β-nitrostyrenes, via an unprecedented reaction sequence.
TLDR
An unprecedented mechanism involving sequential indole dimerization, regioselective nucleophilic conjugate addition of the resulting 2,3'-biindole to β-nitrostyrene and formal intramolecular [4 + 2]-cycloaddition is proposed.
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References

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α-chloro ketoximes as precursors of nitrosoalkenes: preparation, stereochemistry, and conformation
Les α-chlorocetoximes conduisent facilement aux mitosoalcenes avec la triethylamine alors que les α-chlorosilyloximes traites par le fluorure de tetrabutylammonium sont moins efficaces
Construction of bridged and fused ring systems via intramolecular Michael reactions of vinylnitroso compounds.
TLDR
Malonate anions have proven to be effective carbon nucleophiles in these conjugate addition reactions, and simple ester potassium enolates have also been successfully employed.
The vinylogous anomeric effect in 3-alkyl-2-chlorocyclohexanone oximes and oxime ethers
A series of trans-3-alkyl-2-chlorocyclohexanones, (methyl, ethyl, isopropyl, and tert-butyl), have been prepared and shown to exist predominantly in the diequatorial chair conformation except the
Intramolecular [4+2] cycloadditions of nitrosoalkenes with olefins
The intmmolecular (4+2)-cycloadditions of di- and uisubstimtcd niaoalkenes with tinactivated oletins arc described. The cycleadditions proceed readily at low temperatures in the presence of S&14. The
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