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1.
Chem Commun (Camb) ; 47(18): 5286-8, 2011 May 14.
Artigo em Inglês | MEDLINE | ID: mdl-21451851

RESUMO

Mesoporous silica grafted with a tertiary amine was used as a basic nanocatalyst to promote in confined medium the enantioselective cascade rearrangement of enediynes based on the phenomenon of memory of chirality; the multi-substrates recyclable catalytic reagent could easily be recovered by simple filtration, and reused without any decrease in activity even when changing the solvent.

2.
J Am Chem Soc ; 132(42): 14742-4, 2010 Oct 27.
Artigo em Inglês | MEDLINE | ID: mdl-20879786

RESUMO

The cascade rearrangement of chiral enediynes 1c-e, involving successively 1,3-proton shift, Saito-Myers cyclization, 1,5-hydrogen atom transfer, and intramolecular coupling of the resulting biradical, proceeded at 80 °C to form tri- and tetracyclic heterocycles possessing a quaternary stereogenic center with a very high level of memory of chirality.


Assuntos
Enedi-Inos/química , Ciclização , Modelos Moleculares , Estereoisomerismo
3.
Org Lett ; 12(16): 3590-3, 2010 Aug 20.
Artigo em Inglês | MEDLINE | ID: mdl-20666447

RESUMO

Dimethylzinc-mediated addition of acyloxymethyl radicals to diethyl fumarate led to the highly stereoselective formation of disubstituted gamma-lactones in mean to good yields; this cascade provides a new example of a one-pot process mediated by dimethylzinc involving a tandem radical-anionic reaction; the chemoselectivity of the reaction was totally modified by additional Lewis acids.

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