Producción Científica Profesorado

r-Alkylation of (S)-Asparagine with Self-Regeneration of the Stereogenic Center: Enantioselective Synthesis of r-Substituted Aspartic Acids



Lopez Ruíz, Heraclio

1998

E. Juaristi, Heraclio López-Ruiz, D. Madrigal, Y. Ramírez-Quirós y J. Escalante, a-Alkylation of (S)-Asparagine with Self-Regeneration of the Stereogenic Center: Enantioselective Synthesis of a-Substituted Aspartic Acids, J. Org. Chem., 63, 4706-4710 (1998).


Abstract


A convenient method for the R-alkylation of (S)-asparagine with self-regeneration of the stereogenic center is described. The synthetic protocol involves stereoselective conversion of (S)-asparagine into enantiopure imino ether (2S,6S)-9, which is then alkylated with complete diastereoselectivity to give trans products 10-13 in good yields. Hydrolysis of these alkylated heterocycles is accomplished under mild acidic conditions to give the desired, enantiopure R-alkyl aspartic acids in excellent yields.



Producto de Investigación




Artículos relacionados

Ylidaddukte der Penteltrichloride

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

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

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

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

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

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

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

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

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