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


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).


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

Facile synthesis of 1,3,6-oxadiazepines from 2,2?-(1,2-ethanediyldiimino)bisphenols

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

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

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

Diastereoselective Synthesis of Spiro-?-lactams via Staudinger Reaction

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

The Structural Chemistry of N-Monolithium Borazines

Study of the reactivity of squarylferrocenes. Addition of amines and aminoesters

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

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