Producción Científica Profesorado

Synthesis of new homochiral 2,3-dialkylpiperazines derived from (R)-(?)-phenylglycinol



Rojas Lima, Susana

2001

Victor Florencio Santes, Elizabeth Gómez Pérez, Verónica Zárate, Rosa Luisa Santillán Baca, José Norberto Farfán García, Susana Rojas-Lima. Synthesis of new homochiral 2,3-dialkylpiperazines derived from (R)-(-)-phenylglycinol Tetrahedron: Asymmetry, 12, 241-247 (2001). DOI: http://dx.doi.org/10.1016/S0957-4166(01)00036-2


Abstract


The synthesis of four new 2,3-dialkylpiperazines in yields of 7099% using (R)-(?)-phenylglycinol as a chiral inductor is described. The synthesis involved reduction of the oxazinooxazine type derivatives obtained by condensation of glyoxal and phenylglycinol to give hydroxyethylenediamine precursors which were further condensed with glyoxal, butanedione and 1-phenyl-1,2-propanedione and then reduced to provide the corresponding piperazines. The stereochemical outcome is determined by the configuration of the bisoxazolidine precursors, which is in turn dictated by steric effects exerted by the substituents on the five membered ring. The structures of five derivatives were established by X-ray analysis.



Producto de Investigación




Artículos relacionados

New boronates prepared from 2,4-pentanedione derived ligands of the NO2 and N2O2 type comparison to...

Highly diastereoselective alkylation, acylation and aldol condensation of cis- and trans-(N-acyloyl)...

Comparative Structural Characterization of the Biquaternized N-CH3 and N-BH3 Derivatives of the cis-...

Enantioselective synthesis of ?-amino acids. Part 10: Preparation of novel ?,?- and ?,?-disubstitute...

Aroylthioureas: new organic ionophores for heavy-metal ion selective electrodes

Ylidaddukte der Penteltrichloride

Synthesis of nitrogen-, oxygen- and sulphur-containing tripodal ligands with a trimethylbenzene core...

Addition reaction of benzylbenzylidenenamine to lithium enolates of 1,3-dioxolan-4-one: synthesis of...

Preparation of Seven- and Eight-Membered Boron Heterocycles from Different Salen Ligands and Arylbor...

Further insight into three center hydrogen bonding. Participation in tautomeric equilibria of hetero...