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

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

Synthesis of nitrogen-, oxygen- and sulphur-containing tripodal ligands with a trimethylbenzene core...

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

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

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

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

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

Synthesis of new homochiral 2,3-dialkylpiperazines derived from (R)-(?)-phenylglycinol

Stereoselective addition of allylmagnesium chloride to the CN bond of [4.3.0] boron heterobicycles

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