Stereoselective geminal difunctionalization of vinyl arenes mediated by the bromonium ion.

@article{Balaji2014StereoselectiveGD,
  title={Stereoselective geminal difunctionalization of vinyl arenes mediated by the bromonium ion.},
  author={Pandur Venkatesan Balaji and Srinivasan Chandrasekaran},
  journal={Chemical communications},
  year={2014},
  volume={50 1},
  pages={
          70-2
        }
}
An anti-Markovnikov geminal oxyamination of styrenyl alkenes in an intermolecular fashion using the umpolung strategy mediated by the bromonium ion is reported. Isotope labeling studies confirm the migration of the phenyl group in the semipinacol rearrangement. 
View on PubMed
rsc.org
12 Citations

Figures and Tables from this paper

12 Citations

Citation Type

Citation Type

Stereoselective Anti‐Markovnikov Geminal Diamination and Dioxy­gena­tion of Vinylarenes Mediated by the Bromonium Ion
A straightforward method is reported for the stereoselective anti-Markovnikov geminal diamination and stoichiometric geminal dioxygenation of vinylarenes mediated by a bromonium ion. The role of the…
Electrochemical tandem trifluoromethylation of allylamines/formal (3 + 2)-cycloaddition for the rapid access to CF3-containing imidazolines and oxazolidines
A straightforward and environmentally friendly synthesis of CF3-containing imidazolines and oxazolidines has been developed through an electrochemical three-component reaction among allylamines, the…
Divergent synthesis of oxazolidines and morpholines via PhI(OAc)2-mediated difunctionalization of alkenes.
TLDR
The PhI(OAc)2-mediated 1,1- and 1,2-difunctionalization of alkenes with N-tosyl amino alcohols to form oxazolidine and morpholine derivatives was realized under mild reaction conditions and allows application to various substrates furnishing the multi-substitutedOxazolidines and morpholines with yields up to 98%.
Iridium-catalyzed direct synthesis of tryptamine derivatives from indoles: exploiting n-protected β-amino alcohols as alkylating agents.
The selective C3-alkylation of indoles with N-protected ethanolamines involving the "borrowing hydrogen" strategy is described. This method provides convenient and sustainable access to several…
Conversion of aziridines to oxazolidines through geminal difunctionalization of vinyl arenes or by tandem ring-opening/closing reaction of aziridine itself
Reagent-switch controlled metal-free intermolecular geminal diamination and aminooxygenation of vinylarenes
Chiral Organotin-Catalyzed Kinetic Resolution of Vicinal Amino Alcohols.
TLDR
A highly efficient kinetic resolution of racemic amino alcohols has been achieved for the first time with a chiral tin catalyst, affording the corresponding products in high enantioselectivity and with s factors up to > 500.
The use of N-halosuccinimides for cyclization with the formation of five-membered heterocyclic compounds
The review summarizes the literature data for the period 2000–2017 on the most successful use of N-halosuccinimides in the preparative synthesis of five-membered heterocyclic compounds. The review is…
An Efficient Synthesis of Oxazolidines by Tandem Ring-Opening / Closing Reaction of Ts-Aziridine Using Formic Acid
Oxazolidine and its derivatives are very important compounds due to their various pharmacological activities such as antitumor, cytotoxic, anti-inflammatory, analgesic properties and they appear in…
Recent progress of 1,1-difunctionalization of olefins.
TLDR
This minireview provides a brief overview of the advancements of 1,1-difunctionalization of olefins in the past twenty years, and prospects of future developments.
...
1
2
...

References

SHOWING 1-10 OF 44 REFERENCES
NaIO4/LiBr-mediated diastereoselective dihydroxylation of olefins: a catalytic approach to the Prevost-Woodward reaction.
TLDR
LiBr catalyzes efficiently the dihydroxylation of alkenes to afford syn and anti diols with excellent diastereoselectivity depending upon the use of NaIO(4) or PhI(OAc)(2) (1 equiv) as the oxidants.
A generalized approach for iron catalyzed chemo- and regioselective formation of anti-Markovnikov acetals from styrene derivatives.
Fe(BF(4))(2)·6H(2)O in the presence of pyridine-2,6-dicarboxylic acid and PhI(OAc)(2) can efficiently catalyze the formation of chemoselective dialkyl acetals from styrene derivatives with…
Metal-free oxyaminations of alkenes using hydroxamic acids.
TLDR
A radical-mediated approach to metal-free alkene oxyamination using simple diisopropyl azodicarboxylate (DIAD) as a radical trap to furnish a general difunctionalization of cyclic alkenes, providing single regioisomers in all cases.
Enantioselective synthesis of 2-substituted and 3-substituted piperidines through a bromoaminocyclization process.
TLDR
A catalytic enantioselective bromocyclization of olefinic amides using amino-thiocarbamates as the catalysts has been developed and has been applied to the synthesis of a dopaminergic drug, Preclamol.
Highly stereoselective metal-free oxyaminations using chiral hypervalent iodine reagents.
TLDR
A highly enantioselective oxyamination of alkenes with N-sulfonyl ureas employing chiral, lactic acid-based hypervalent iodine reagents gives a facile synthesis of enantiomerically pure 2-arylproline derivatives for the first time.
Pd(II)-catalyzed conversion of styrene derivatives to acetals: impact of (-)-sparteine on regioselectivity.
TLDR
Initial mechanistic studies indicate that the reaction proceeds through an enol ether intermediate and a Pd-hydride, which indicates that the substrate scope of this reaction has been investigated.
Stereoselective rearrangements with chiral hypervalent iodine reagents.
TLDR
For the first time, rearrangements to α-arylated ketones can be performed enantioselectively using lactic acid-based iodine(III) reagents.
2,2-Difunctionalization of alkenes via Pd(II)-catalyzed aza-Wacker reactions.
TLDR
N-Ts and N-Boc derivatives of 1,2-diamines and 1-2-amino alcohols are shown to undergo efficient Pd(II)-catalyzed aza-Wacker reactions with a large range of electron-deficient alkenes, which facilitates the rapid synthesis of saturated oxazolidines, imidazolidine, and their derivatives.
Metal-free highly regioselective aminotrifluoroacetoxylation of alkenes.
TLDR
A highly regioselective metal-free oxidative cyclization of sulfonamides onto tethered, unactivated alkenes using hypervalent iodine and Brønsted acids and an unusual preference for endo ring closure is exhibited in contrast to existing exo selective methods.
A facile preparation of 2-arylpropionaldehyde from 1-aryl-1-propene
1-Aryl-1-propenes were converted into the corresponding 2-arylpropionaldehydes in high yields by treatment with iodine and silver(I)oxide in aqueous dioxane at room temperature.
...
1
2
3
4
5
...