The stereospecific lithiation of diastereomeric phenylpropylene oxides has been studied as well a... more The stereospecific lithiation of diastereomeric phenylpropylene oxides has been studied as well as the trapping reaction with electrophiles. The reduction of the cis-alpha-benzoylpropylene oxide to give prevalently the anti-epoxy alcohol has been investigated as well.
The stereospecific lithiation of diastereomeric phenylpropylene oxides has been studied as well a... more The stereospecific lithiation of diastereomeric phenylpropylene oxides has been studied as well as the trapping reaction with electrophiles. The reduction of the cis-alpha-benzoylpropylene oxide to give prevalently the anti-epoxy alcohol has been investigated as well.
[reaction: see text] A stereoselective/stereospecific synthesis of polysubstituted tetrahydronaph... more [reaction: see text] A stereoselective/stereospecific synthesis of polysubstituted tetrahydronaphthols based on the Michael addition of ortho-lithiated stilbene oxides to alpha,beta-unsaturated Fischer carbene complexes followed by an unusual cyclization of the corresponding intermediate in a 6-endo-tet mode is described.
The synthesis of terminal oxazolinyloxiranes, even in enantioenriched form, has been performed by... more The synthesis of terminal oxazolinyloxiranes, even in enantioenriched form, has been performed by Darzens-type reaction of lithiated chloroalkyloxazolines with benzotriazolylmethanol (BtCH2OH) or by chloromethylation of 2-acyl-2-oxazolines. The ...
A short and efficient synthesis of tetrahydroindenofuranones based on the Michael addition of ort... more A short and efficient synthesis of tetrahydroindenofuranones based on the Michael addition of ortho-lithiated aryloxiranes to alkylidene malonates followed by the nucleophilic oxirane ring-opening and subsequent lactonization is described. The methodology has been applied to the synthesis of a structural analogue of epipodophyllotoxins.
Saverio Florio received his Laurea in Chemistry at the University of Bari (Italy) and started h... more Saverio Florio received his Laurea in Chemistry at the University of Bari (Italy) and started his academic career there, first as Assistant Professor (1969) and then as Associate Professor of Organic Chemistry (1982). In 1986, he was appointed Full Professor of ...
The reaction of α-lithiated-2-alkyl-2-oxazolines 1-Li with aliphatic, aromatic and heteroaromatic... more The reaction of α-lithiated-2-alkyl-2-oxazolines 1-Li with aliphatic, aromatic and heteroaromatic N-cumyl nitrones results in the stereoselective formation of N-cumyl-1, 6-dioxa-2, 9-diazaspiro [4, 4] nonanes 3 which equilibrate with the hydroxylamino ...
[structure: see text]. The lithiation reaction of cis- and trans-N-alkyl-2,3-diphenylaziridines h... more [structure: see text]. The lithiation reaction of cis- and trans-N-alkyl-2,3-diphenylaziridines has been investigated. While cis-diphenylaziridines do not undergo any lithiation upon treatment with organolithiums, the lithiation reaction of the trans counterparts is completely alpha-regioselective and the stereochemical course of the lithiation-trapping sequence is solvent dependent: inversion of configuration in coordinating solvents (THF or toluene/crown ether) and retention in hexane, ether, or toluene. The preparation of stereodefined functionalized N-alkyl-2,3-diphenylaziridines is described.
A general method for the synthesis of 2,3-dihydro-10bH-oxazolo[2,3-a]isoquinolines from the react... more A general method for the synthesis of 2,3-dihydro-10bH-oxazolo[2,3-a]isoquinolines from the reaction of (R*,R*)-configured ortho-bromophenyloxazolinyloxiranes and organolithiums is described.
The stereospecific lithiation of diastereomeric phenylpropylene oxides has been studied as well a... more The stereospecific lithiation of diastereomeric phenylpropylene oxides has been studied as well as the trapping reaction with electrophiles. The reduction of the cis-alpha-benzoylpropylene oxide to give prevalently the anti-epoxy alcohol has been investigated as well.
The stereospecific lithiation of diastereomeric phenylpropylene oxides has been studied as well a... more The stereospecific lithiation of diastereomeric phenylpropylene oxides has been studied as well as the trapping reaction with electrophiles. The reduction of the cis-alpha-benzoylpropylene oxide to give prevalently the anti-epoxy alcohol has been investigated as well.
[reaction: see text] A stereoselective/stereospecific synthesis of polysubstituted tetrahydronaph... more [reaction: see text] A stereoselective/stereospecific synthesis of polysubstituted tetrahydronaphthols based on the Michael addition of ortho-lithiated stilbene oxides to alpha,beta-unsaturated Fischer carbene complexes followed by an unusual cyclization of the corresponding intermediate in a 6-endo-tet mode is described.
The synthesis of terminal oxazolinyloxiranes, even in enantioenriched form, has been performed by... more The synthesis of terminal oxazolinyloxiranes, even in enantioenriched form, has been performed by Darzens-type reaction of lithiated chloroalkyloxazolines with benzotriazolylmethanol (BtCH2OH) or by chloromethylation of 2-acyl-2-oxazolines. The ...
A short and efficient synthesis of tetrahydroindenofuranones based on the Michael addition of ort... more A short and efficient synthesis of tetrahydroindenofuranones based on the Michael addition of ortho-lithiated aryloxiranes to alkylidene malonates followed by the nucleophilic oxirane ring-opening and subsequent lactonization is described. The methodology has been applied to the synthesis of a structural analogue of epipodophyllotoxins.
Saverio Florio received his Laurea in Chemistry at the University of Bari (Italy) and started h... more Saverio Florio received his Laurea in Chemistry at the University of Bari (Italy) and started his academic career there, first as Assistant Professor (1969) and then as Associate Professor of Organic Chemistry (1982). In 1986, he was appointed Full Professor of ...
The reaction of α-lithiated-2-alkyl-2-oxazolines 1-Li with aliphatic, aromatic and heteroaromatic... more The reaction of α-lithiated-2-alkyl-2-oxazolines 1-Li with aliphatic, aromatic and heteroaromatic N-cumyl nitrones results in the stereoselective formation of N-cumyl-1, 6-dioxa-2, 9-diazaspiro [4, 4] nonanes 3 which equilibrate with the hydroxylamino ...
[structure: see text]. The lithiation reaction of cis- and trans-N-alkyl-2,3-diphenylaziridines h... more [structure: see text]. The lithiation reaction of cis- and trans-N-alkyl-2,3-diphenylaziridines has been investigated. While cis-diphenylaziridines do not undergo any lithiation upon treatment with organolithiums, the lithiation reaction of the trans counterparts is completely alpha-regioselective and the stereochemical course of the lithiation-trapping sequence is solvent dependent: inversion of configuration in coordinating solvents (THF or toluene/crown ether) and retention in hexane, ether, or toluene. The preparation of stereodefined functionalized N-alkyl-2,3-diphenylaziridines is described.
A general method for the synthesis of 2,3-dihydro-10bH-oxazolo[2,3-a]isoquinolines from the react... more A general method for the synthesis of 2,3-dihydro-10bH-oxazolo[2,3-a]isoquinolines from the reaction of (R*,R*)-configured ortho-bromophenyloxazolinyloxiranes and organolithiums is described.
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