Producción Científica Profesorado

Addition reaction of benzylbenzylidenenamine to lithium enolates of1,3-dioxolan-4-one: synthesis of 2-phenylisoserines



Rojas Lima, Susana

2011

Lizbeth Juárez-Guerra, Susana Rojas-Lima,* and Heraclio López-Ruiz Addition reaction of benzylbenzylidenenamine to lithium enolates of 1,3-dioxolan-4-one: synthesis of 2-phenylisoserines ARKIVOC 2011 (ix) 354-366. Preprinted


Abstract


The synthesis of two new 2-phenylisoserines, each bearing a quaternary stereocenter is described. These compounds, which are analogs of the amino acid side chain found in taxol and taxotere, were obtained by addition of the lithium enolates of (2S,5S)-2-isopropyl-5-phenyl-1,3-dioxolan-4-one and (2S,5S)-2-tert-butyl-2-methyl-5-phenyl-1,3-dioxolan-4-one to benzylbenzylideneamine in the presence of BF3 .O(Et)2. The diastereomeric mixtures were separated in each case and the absolute configurations thereof were determined by X-ray analysis.



Producto de Investigación




Artículos relacionados

Diastereomeric C-glycosyloxanthrones from picramnia antidesma

Synthesis and Structures of some Lithium and Sodium (Aminoalcoholato)hydrido Aluminates

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

r-Alkylation of (S)-Asparagine with Self-Regeneration of the Stereogenic Center: Enantioselective Sy...

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

Facile synthesis of 1,3,6-oxadiazepines from 2,2?-(1,2-ethanediyldiimino)bisphenols

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

Cathepsins X and B Can Be Differentiated through Their Respective Mono- and Dipeptidyl Carboxypeptid...

Bis(acetylsalicylato-j2O,O00)diaquacadmium(II)

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