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

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

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

An efficient potassium cyanide-promoted synthesis of 2-arylbenzoxazoles from [4.3.0]boron heterobicy...

Study of the reactivity of squarylferrocenes. Addition of amines and aminoesters

Et3, and efficient Mediator for Xanthate Transfer Based Radical Processes.

Diastereoselective alkylation of chiral glycinate derivatives containing the ?-phenylethyl group.

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

Effect of TiO2Al2O3 SolGel Supports on the Superficial Ni and Mo Species in Oxidized and Sulfided Ni...

Preparation of N-aryl-substituted spiro-?-lactams via Staudinger cycloaddition

Synthesis and Study of Monomeric and Dimeric Boronates by Spectroscopic Methods and X-ray Crystallog...