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

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

Furocoumarins of three species of the genus Dorstenia

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

Addition reaction of benzylbenzylidenenamine to lithium enolates of 1,3-dioxolan-4-one: synthesis of...

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

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

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

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

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

Ylidaddukte der Penteltrichloride