Facially selective and regioselective carbometalation of cyclopropenes by aryl Grignard reagents.

@article{Yan2008FaciallySA,
  title={Facially selective and regioselective carbometalation of cyclopropenes by aryl Grignard reagents.},
  author={Ni Yan and Xiaozhong Liu and Joseph M. Fox},
  journal={The Journal of organic chemistry},
  year={2008},
  volume={73 2},
  pages={
          563-8
        }
}
Described is a Cu-catalyzed methodology for adding aryl Grignard reagents to 3-hydroxymethylcyclopropene derivatives with high regio- and diastereoselectivity. The cyclopropylmetals can be trapped with a variety of electrophiles to generate highly substituted cyclopropanes. 
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36 Citations

36 Citations

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Citation Type

Regio- and Diastereoselective Copper-Catalyzed Carbometalation of Cyclopropenylsilanes.
We therein report a regio- and diastereoselective copper-catalyzed carbometalation of enantioenriched readily available cyclopropenylsilanes as a synthetic tool to access a large family of…
Regio- and Diastereoselective Copper-Catalyzed Carbomagnesiation for the Synthesis of Penta- and Hexa-Substituted Cyclopropanes.
Despite the highly strained nature of cyclopropanes possessing three vicinal quaternary carbon stereocenters, the regio- and diastereoselective copper-catalyzed carbomagnesiation reaction of…
Diastereo- and enantioselective copper catalyzed hydroallylation of disubstituted cyclopropenes
A highly diastereo- and enantioselective protocol for the hydroallylation of 1,1- and 1,2-disubstituted cyclopropenes has been developed utilizing an in situ formed copper hydride.
Facially selective Cu-catalyzed carbozincation of cyclopropenes using arylzinc reagents formed by sequential I/Mg/Zn exchange.
TLDR
A Cu-catalyzed directed carbozincation of cyclopropenes with organozinc reagents prepared by I/Mg/Zn exchange broadens the scope with respect to functional group tolerance and enables use of aryl iodide precursors, rather than purified diorganozinc precursor.
Enantioselective synthesis of cyclopropylcarboxamides using s-BuLi-sparteine-mediated metallation.
Enantioselective synthesis of cyclopropylcarboxamides is possible by asymmetric metallation of prochiral starting cyclopropanes using s-BuLi-sparteine.
Stereospecific synthesis of alkylidenecyclopropanes via sequential cyclopropene carbomagnesation/1,3-carbon shift.
Alkylidenecyclopropanes can be synthesized from enantiomerically enriched cyclopropene derivatives with >99% stereotransfer and good to excellent yield. The protocol comprises the stereoselective…
Cyclopropene-Templated Assembly of Medium Cycles via Ru-Catalyzed Ring-Closing Metathesis.
TLDR
An expeditious click-click cyclize strategy for the assembly of medium-sized heterocyclic rings is described, which allows for the efficient preparation of lactams with ring sizes up to 10.
Unique reactivity of Grignard reagents towards cyclopropenyl-carboxylates—highly selective carbon–carbon bond cleavage
An unexpected highly selective reaction of Grignard reagents is described: Instead of generating the normal tertiary alcohols from the reaction with the ester functionality, its treatment with doubly…
Formation of Carbocycles via a 1,4-Rh Shift Triggered by a Rhodium-Catalyzed Addition of Terminal Alkynes to 3,3-Diarylcyclopropenes.
The catalytic addition of terminal alkynes to 3,3-diarylcyclopropenes in the presence of a Rh(I)/binap complex proceeded to give the cycloaddition products in good yields, where a 1,4-Rh shift is…
Unexpected regioselectivity switch: organophosphine-triggered reactions of cyclopropene-1,1-dicarboxylates with aldehydes.
With tris(4-methoxyphenyl)phosphine as the nucleophilic reagent, the readily available cyclopropene-1,1-dicarboxylates undergo a ring-opening reaction to generate a Wittig-type intermediate, which…
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