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

O-benzyl-N-(2-furoyl)thiocarbamate

Diastereoselective Synthesis of Spiro-?-lactams via Staudinger Reaction

Structure-Activity Relationships for Inhibition of Cysteine Protease Activity and Development of Pla...

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

X-ray crystallographic study of neutral boron chelates with ?-diketones and tropolone

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

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

3-Benzoyl-2-isopropyl-4-alkyloxazolidin-5-ones as Efficient and Inexpensive Sources of Enantiopure ?...

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

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