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

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

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

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

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

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

Highly diastereoselective alkylation, acylation and aldol condensation of cis- and trans-(N-acyloyl)...

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

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

Enantioselective synthesis of ?-amino acids. Part 10: Preparation of novel ?,?- and ?,?-disubstitute...

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