Producción Científica Profesorado

Addition reaction of benzylbenzylidenenamine to lithium enolates of 1,3-dioxolan-4-one: synthesis of 2-phenylisoserines



Lopez Ruíz, Heraclio

2011

Lizbeth Juárez-Guerra, Susana Rojas-Lima,* y 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

Synthesis and Study of Isomeric Benzo[1,4]oxazines and Benzothiazolines by NMR Spectroscopy and X-Ra...

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

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

Diastereoselective Synthesis of Spiro-?-lactams via Staudinger Reactio

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

Diastereoselective Synthesis of Spiro-?-lactams via Staudinger Reaction

Synthesis, crystal structures, and quadratic nonlinear optical properties in a series of pushpull bo...

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

Furocoumarins of three species of the genus Dorstenia

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