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

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

Diastereoselective Synthesis of Spiro-?-lactams via Staudinger Reactio

Synthesis of New Chiral Derivatives of N,N?-Dimethylpropyleneurea (DMPU) and Examination of Their In...

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

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

Et3B, an Efficient Mediator for Xanthate Transfer Based Radical Processes

Structural studies of spiroarsoranes derived from 2-aminophenols

Phenylboronic acid catalyzed-cyanide promoted, one-pot synthesis of 2-(2-hydroxyphenyl)benzoxazole d...

Phenylmethyl 2,3,4-tri-O-acetyl--D-fucopyranoside

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