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

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

Enantioselective synthesis of ?-amino acids. Part 11: Diastereoselective alkylation of chiral deriva...

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

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

Aroylthioureas: new organic ionophores for heavy-metal ion selective electrodes

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

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

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

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

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