Vito Capriati

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 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 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 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 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 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 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.

[reaction: see text] A stereoselective synthesis of 9,10-epoxy-1,6-dioxa-4,7-diazaspiro[4,5]decanes has been developed on the basis of the addition of beta-lithiated oxazolinyloxiranes to nitrones. Conversion of these spirocyclic derivatives into 4,5-epoxy-1,2-oxazin-6-ones and successively into alpha,beta-epoxy-gamma-amino acids, alpha-hydroxy-gamma-amino acids, and gamma-butyrolactams is described.

... α-Lithiated Aryloxiranes: Useful Reactive Intermediates. Vito Capriati,; Saverio Florio,; Renzo Luisi. Article first published online: 31 AUG 2005. ... [75 refs.]. Vito Capriati, Saverio Florio, Renzo Luisi, α-Lithiated Aryloxiranes: Useful Reactive Intermediates, Synlett, 2005, 1359–1369. ...

[reaction: see text] The stereoselective synthesis of novel alpha-epoxy-beta-amino acids is described by a route that combines the chemistry of oxazolinyloxiranyllithiums with that of nitrones. The intermediate trioxadiazadispiro[2.0.4.3]undecanes 4 have been isolated and converted by hydrolysis into epoxy-5-isoxazolidinones 5 which can be transformed into the alpha-epoxy-beta-amino acids 8 by N-O reduction.

The addition reaction of α-lithiated oxazolinyloxiranes to nitrones has been investigated. 1, 5, 9-Trioxa-8, 10-diazadispiro [2.0. 4.3] undecanes formed in a completely diastereoselective manner upon treatment of α-lithiated oxiranes with nitrones. The ...

2-chloroalkylbenzothiazoles 1a-c react with alkoxides to give substitution and ring-expanded products 3 and 4. The substitution ring-enlargement competition much depends upon the solvent, the substitution reaction being preferred in alcohols and the ring-...

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Abstract Deprotonation of oxazolinyloxiranes 1a, 1h, and 1k with sBuLi/TMEDA at–100 C in Et 2 O furnishes oxazolinyloxiranyllithium compounds [1] 1b, 1i, and 1l which are stable at low temperature and can be trapped with electrophiles to give substituted oxiranes 1c–1g ...

[reaction: see text] A stereoselective synthesis of 9,10-epoxy-1,6-dioxa-4,7-diazaspiro[4,5]decanes has been developed on the basis of the addition of beta-lithiated oxazolinyloxiranes to nitrones. Conversion of these spirocyclic derivatives into 4,5-epoxy-1,2-oxazin-6-ones and successively into alpha,beta-epoxy-gamma-amino acids, alpha-hydroxy-gamma-amino acids, and gamma-butyrolactams is described.