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Papers by Liliana Marzorati
Organic Letters, 2014
Apart from their exotic structure, radialenes have been employed as precursors of more complex po... more Apart from their exotic structure, radialenes have been employed as precursors of more complex polycyclic molecules. In this work we report the synthesis of the first compound having the benzo[5]radialene substructure, starting from simple materials. Such a compound proved to be a convenient diene in Diels-Alder reactions, for the preparation of highly functionalized fluorenes and benzo[b]fluorenes in a quimio- and stereocontrolled fashion.
Tetrahedron: Asymmetry, 2012
Synthesis, 2013
ABSTRACT alpha-Sulfanylated alpha-arylacetates and -thioacetates were prepared via ethylthiomethy... more ABSTRACT alpha-Sulfanylated alpha-arylacetates and -thioacetates were prepared via ethylthiomethylation reaction of aromatic compounds. These aromatic electrophilic substitutions were performed by in situ generation of the thionium ions by reacting trifluoroacetic anhydride and S-ethyl 2-(ethylsulfinyl)ethanethioate or ethyl 2-(ethylsulfinyl) acetate in the presence of Lewis acids. Some mechanistic features of these ethylthiomethylation reactions are also presented.
Tetrahedron Letters, 2007
Tetrahedron Letters, 2010
Increased diastereoisomeric excesses are obtained for the sulfanylation reactions of some 2-methy... more Increased diastereoisomeric excesses are obtained for the sulfanylation reactions of some 2-methylsulfinyl cyclanones under phase-transfer catalysis using the chiral catalyst QUIBEC instead of TEBA. The optically pure (SS,2S)-2-methylsulfinyl-2-methylsulfanylcyclohexanone thus prepared reacts with ethyl acetate lithium enolate affording, after hydrolysis, (R)-2-[(ethoxycarbonyl)methyl]-2-hydroxycyclohexanone in 60% ee. Density functional theory calculations (at the B3LYP/6-311++G(d,p) level) can successfully explain the origin of this result as the kinetically favored axial attack of the nucleophile to the carbonyl group of the most stable conformer of the cyclanone, in which the CH 3 SO and CH 3 S groups are at the equatorial and axial positions, respectively.
Tetrahedron, 1999
The asymmetric induction in the suifenylation of several I~-kcto sulfoxides under phase transfer ... more The asymmetric induction in the suifenylation of several I~-kcto sulfoxides under phase transfer catalytic conditions in the presence of the chiral catalyst N-bcnzylquininium chloride was investigated. It is concluded that the diutereo~lect3vity is not accompanied by eaantiomaric resolution.
Synthetic Communications, 1998
Synthetic Communications, 2010
... DOI: 10.1080/00397910902962852 Claudio L. Donnici a * , Elaine Henriques Teixeira Pereira a ,... more ... DOI: 10.1080/00397910902962852 Claudio L. Donnici a * , Elaine Henriques Teixeira Pereira a , Júlio C. Dias Lopes a , Liliana Marzorati b & Blanka Wladislaw b pages 342-350. ... [CrossRef], [Web of Science ®] View all references ] Interestingly, Corey, and Lowry reported an ...
Synthetic Communications, 2002
Addition of thiols or diethylmalonate to thiocinnamate, under solid–liquid PTC conditions, afford... more Addition of thiols or diethylmalonate to thiocinnamate, under solid–liquid PTC conditions, afforded the corresponding 1,4-adducts in moderate to good yields. A 2-pyrrolidinone was obtained using diethyl N-acetamidomalonate as Michael donor, via intramolecular cyclization of the parent adduct.
Synthetic Communications, 1996
Synthetic Communications, 2003
ABSTRACT
Synthetic Communications, 2002
α-Phenylsulfonyl methylthioacetate gave monoalkylated products in high yields when treated with a... more α-Phenylsulfonyl methylthioacetate gave monoalkylated products in high yields when treated with alkyl halides in the presence of K2CO3 with TEBAC in CH2Cl2, at r.t. The superiority of this method over that in the homogeneous phase is discussed.
Synthetic Communications, 2000
Química Nova, 1999
ABSTRACT
Phosphorus, Sulfur, and Silicon and the Related Elements, 1997
Page 1. Phosphoms, S ulfu ~ and Silicon, 1997, Vol. 123, pp. 197-208 Reprinls available directly ... more Page 1. Phosphoms, S ulfu ~ and Silicon, 1997, Vol. 123, pp. 197-208 Reprinls available directly from the pubhsher Photocopying permitted by license only 0 1997 OPA (Overseas Publishers Association) Amsterdam BV Published ...
Phosphorus, Sulfur, and Silicon and the Related Elements, 2000
Some β-keto sulfoxides containing different groups at the sulfinyl moiety were submitted to sulfe... more Some β-keto sulfoxides containing different groups at the sulfinyl moiety were submitted to sulfenylation reaction employing two procedures: in homogeneous media and by PTC to give the corresponding monosulfenylated products. The Z configuration for the enolates of the β-keto sulfoxides independently of the group at the sulfur moiety is proved by H NMR NOE difference experiments. The diastereoselectivity observed in
Phosphorus, Sulfur, and Silicon and the Related Elements, 2003
The sulfanylation of methyl dimethylphosphonothioacetate was investigated by a phase transfer cat... more The sulfanylation of methyl dimethylphosphonothioacetate was investigated by a phase transfer catalysis procedure which was shown to be superior to the noncatalytic method. The possibility of electrophilic substitution of the α-sulfanylated phosphonothioacetate to give a quaternary α-carbon atom is shown by the reaction with methyl iodide.We thank Fundação de Amparo à Pesquisa do Estado de São Paulo for financial support
Phosphorus, Sulfur, and Silicon and the Related Elements, 1996
Some α-methylsulfanyl phosphorylsulfoxides were obtained by sulfenylation reaction in homogeneous... more Some α-methylsulfanyl phosphorylsulfoxides were obtained by sulfenylation reaction in homogeneous phase.
Organic Letters, 2014
Apart from their exotic structure, radialenes have been employed as precursors of more complex po... more Apart from their exotic structure, radialenes have been employed as precursors of more complex polycyclic molecules. In this work we report the synthesis of the first compound having the benzo[5]radialene substructure, starting from simple materials. Such a compound proved to be a convenient diene in Diels-Alder reactions, for the preparation of highly functionalized fluorenes and benzo[b]fluorenes in a quimio- and stereocontrolled fashion.
Tetrahedron: Asymmetry, 2012
Synthesis, 2013
ABSTRACT alpha-Sulfanylated alpha-arylacetates and -thioacetates were prepared via ethylthiomethy... more ABSTRACT alpha-Sulfanylated alpha-arylacetates and -thioacetates were prepared via ethylthiomethylation reaction of aromatic compounds. These aromatic electrophilic substitutions were performed by in situ generation of the thionium ions by reacting trifluoroacetic anhydride and S-ethyl 2-(ethylsulfinyl)ethanethioate or ethyl 2-(ethylsulfinyl) acetate in the presence of Lewis acids. Some mechanistic features of these ethylthiomethylation reactions are also presented.
Tetrahedron Letters, 2007
Tetrahedron Letters, 2010
Increased diastereoisomeric excesses are obtained for the sulfanylation reactions of some 2-methy... more Increased diastereoisomeric excesses are obtained for the sulfanylation reactions of some 2-methylsulfinyl cyclanones under phase-transfer catalysis using the chiral catalyst QUIBEC instead of TEBA. The optically pure (SS,2S)-2-methylsulfinyl-2-methylsulfanylcyclohexanone thus prepared reacts with ethyl acetate lithium enolate affording, after hydrolysis, (R)-2-[(ethoxycarbonyl)methyl]-2-hydroxycyclohexanone in 60% ee. Density functional theory calculations (at the B3LYP/6-311++G(d,p) level) can successfully explain the origin of this result as the kinetically favored axial attack of the nucleophile to the carbonyl group of the most stable conformer of the cyclanone, in which the CH 3 SO and CH 3 S groups are at the equatorial and axial positions, respectively.
Tetrahedron, 1999
The asymmetric induction in the suifenylation of several I~-kcto sulfoxides under phase transfer ... more The asymmetric induction in the suifenylation of several I~-kcto sulfoxides under phase transfer catalytic conditions in the presence of the chiral catalyst N-bcnzylquininium chloride was investigated. It is concluded that the diutereo~lect3vity is not accompanied by eaantiomaric resolution.
Synthetic Communications, 1998
Synthetic Communications, 2010
... DOI: 10.1080/00397910902962852 Claudio L. Donnici a * , Elaine Henriques Teixeira Pereira a ,... more ... DOI: 10.1080/00397910902962852 Claudio L. Donnici a * , Elaine Henriques Teixeira Pereira a , Júlio C. Dias Lopes a , Liliana Marzorati b & Blanka Wladislaw b pages 342-350. ... [CrossRef], [Web of Science ®] View all references ] Interestingly, Corey, and Lowry reported an ...
Synthetic Communications, 2002
Addition of thiols or diethylmalonate to thiocinnamate, under solid–liquid PTC conditions, afford... more Addition of thiols or diethylmalonate to thiocinnamate, under solid–liquid PTC conditions, afforded the corresponding 1,4-adducts in moderate to good yields. A 2-pyrrolidinone was obtained using diethyl N-acetamidomalonate as Michael donor, via intramolecular cyclization of the parent adduct.
Synthetic Communications, 1996
Synthetic Communications, 2003
ABSTRACT
Synthetic Communications, 2002
α-Phenylsulfonyl methylthioacetate gave monoalkylated products in high yields when treated with a... more α-Phenylsulfonyl methylthioacetate gave monoalkylated products in high yields when treated with alkyl halides in the presence of K2CO3 with TEBAC in CH2Cl2, at r.t. The superiority of this method over that in the homogeneous phase is discussed.
Synthetic Communications, 2000
Química Nova, 1999
ABSTRACT
Phosphorus, Sulfur, and Silicon and the Related Elements, 1997
Page 1. Phosphoms, S ulfu ~ and Silicon, 1997, Vol. 123, pp. 197-208 Reprinls available directly ... more Page 1. Phosphoms, S ulfu ~ and Silicon, 1997, Vol. 123, pp. 197-208 Reprinls available directly from the pubhsher Photocopying permitted by license only 0 1997 OPA (Overseas Publishers Association) Amsterdam BV Published ...
Phosphorus, Sulfur, and Silicon and the Related Elements, 2000
Some β-keto sulfoxides containing different groups at the sulfinyl moiety were submitted to sulfe... more Some β-keto sulfoxides containing different groups at the sulfinyl moiety were submitted to sulfenylation reaction employing two procedures: in homogeneous media and by PTC to give the corresponding monosulfenylated products. The Z configuration for the enolates of the β-keto sulfoxides independently of the group at the sulfur moiety is proved by H NMR NOE difference experiments. The diastereoselectivity observed in
Phosphorus, Sulfur, and Silicon and the Related Elements, 2003
The sulfanylation of methyl dimethylphosphonothioacetate was investigated by a phase transfer cat... more The sulfanylation of methyl dimethylphosphonothioacetate was investigated by a phase transfer catalysis procedure which was shown to be superior to the noncatalytic method. The possibility of electrophilic substitution of the α-sulfanylated phosphonothioacetate to give a quaternary α-carbon atom is shown by the reaction with methyl iodide.We thank Fundação de Amparo à Pesquisa do Estado de São Paulo for financial support
Phosphorus, Sulfur, and Silicon and the Related Elements, 1996
Some α-methylsulfanyl phosphorylsulfoxides were obtained by sulfenylation reaction in homogeneous... more Some α-methylsulfanyl phosphorylsulfoxides were obtained by sulfenylation reaction in homogeneous phase.