Producción Científica Profesorado

Enantioselective synthesis of ?-amino acids. Part 11: Diastereoselective alkylation of chiral derivatives of ?-aminopropionic acid containing the ?-phenethyl group



Lopez Ruíz, Heraclio

2001

V. M. Gutiérrez-García, Heraclio López-Ruiz, G. Reyes-Rangel y E. Juaristi Enantioselective synthesis of b-amino acids. Part 11: Diastereoselective alkylation of Chiral derivatives of b-aminopropionic acids containing the a-phenethyl group. Tetrahedron, 57, 6487-6496 (2001). DOI: http://dx.doi.org/10.1016/S0040-4020(01)00540-3


Abstract


Several novel, chiral derivatives of ?-aminopropionic acid were studied as potentially useful precursors of enantiopure ?-substituted-?-amino acids. In particular, the diastereoselectivity of alkylation of (R,R)-2-Li enolate showed substantial stereoinduction by the bis[?-phenylethyl]amide auxiliary, leading to 80% ds in the methylation reaction. No appreciable effect upon diastereoselectivity was observed by the presence of additives (LiCl, HMPA, DMPU) in the reaction. On the other hand, stereoinduction by the ?-phenylethylamino group in the methylation of ester enolate (S)-3-Li was lower (65% ds) under standard conditions (THF, ?78C) but improved to 81% ds in the presence of 3 equiv. of HMPA as cosolvent. Matched and mismatched derivatives, (R,R,S)-11 and (R,R,R)-11, respectively, were methylated via their corresponding lithium enolates. Observed diastereoselectivities generally followed the anticipated tendencies based on double stereoinduction. Thus diastereoselectivity reached 89% ds in the methylation of the matched isomer, (R,R,S)-11-Li.



Producto de Investigación




Artículos relacionados

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

Further insight into three center hydrogen bonding. Participation in tautomeric equilibria of hetero...

A flexible access to highly functionalised boronates

Ylidaddukte der Penteltrichloride

3-Benzoyl-2-isopropyl-4-alkyloxazolidin-5-ones as Efficient and Inexpensive Sources of Enantiopure ?...

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

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

Synthesis and Structures of some Lithium and Sodium (Aminoalcoholato)hydrido Aluminates

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

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