0000000000178210
AUTHOR
Esther Salavert
ChemInform Abstract: Novel Strategy for the Synthesis of Fluorinated β-Amino Acid Derivatives from Δ2-Oxazolines.
Abstract Racemic and chiral non-racemic β-fluoroalkyl-β-amino acid derivatives have been prepared in two steps starting from 2-alkyl-Δ2-oxazolines and fluorinated imidoyl chlorides. Subsequent chemoselective reduction of the C-masked β-enamino acid derivatives initially formed provided the target β-amino acids. The process takes place with total chemoselectivity, high yields and satisfactory diastereoselectivity.
Novel strategy for the synthesis of fluorinated β-amino acid derivatives from Δ2-oxazolines
Abstract Racemic and chiral non-racemic β-fluoroalkyl-β-amino acid derivatives have been prepared in two steps starting from 2-alkyl-Δ2-oxazolines and fluorinated imidoyl chlorides. Subsequent chemoselective reduction of the C-masked β-enamino acid derivatives initially formed provided the target β-amino acids. The process takes place with total chemoselectivity, high yields and satisfactory diastereoselectivity.
A new and expeditious strategy for the synthesis of β-amino acids from Δ2-oxazolines
Abstract A new, mild two-step synthesis of racemic β-amino acids starting from 2-alkyl-Δ2-oxazolines is described. The process implies the initial formation of masked N-substituted or N-unsubstituted β-enamino acid derivatives followed by chemoselective reduction of the enamino moiety. The process takes place with high yields, total chemoselectivity and moderate diastereoselectivity.
ChemInform Abstract: New Strategy for the Stereoselective Synthesis of Fluorinated β-Amino Acids.
Racemic and chiral nonracemic α-substituted and α-unsubstituted β-fluoroalkyl β-amino acid derivatives 6 and 9 have been synthesized in two steps starting from fluorinated imidoyl chlorides 1 and ester enolates. This approach is based on the chemical reduction of previously obtained γ-fluorinated β-enamino esters 4 by using ZnI2/NaBH4 in a nonchelated aprotic medium (dry CH2Cl2) as the reducing agent. A metal-chelated six-membered model has been suggested to explain the stereochemical outcome of the reduction reaction. The process takes place with high yields and with moderate to good diastereoselectivity. The best results related to diastereoselective reduction of chiral β-enamino esters 4…
An efficient synthesis of new fluorinated uracil derivatives.
A series of potentially biologically active fluorinated uracil derivatives has been prepared in three steps from oxazolines and fluorinated nitriles with good chemical yields. Fustero Lardies, Santos, Santos.Fustero@uv.es ; Sanz Cervera, Juan Francisco, Juan.F.Sanz@uv.es ; Asensio Martinez, Amparo, Amparo.Asensio@uv.es
An efficient synthesis of new fluorinated uracil derivativesElectronic supplementary information (ESI) available: general procedures for the preparation of compounds 3, 6 ,7, 8 and 9. See http://www.rsc.org/suppdata/cc/b3/b300796k/
A series of potentially biologically active fluorinated uracil derivatives has been prepared in three steps from oxazolines and fluorinated nitriles with good chemical yields.
New Strategy for the Stereoselective Synthesis of Fluorinated β-Amino Acids
Racemic and chiral nonracemic alpha-substituted and alpha-unsubstituted beta-fluoroalkyl beta-amino acid derivatives 6 and 9 have been synthesized in two steps starting from fluorinated imidoyl chlorides 1 and ester enolates. This approach is based on the chemical reduction of previously obtained gamma-fluorinated beta-enamino esters 4 by using ZnI(2)/NaBH(4) in a nonchelated aprotic medium (dry CH(2)Cl(2)) as the reducing agent. A metal-chelated six-membered model has been suggested to explain the stereochemical outcome of the reduction reaction. The process takes place with high yields and with moderate to good diastereoselectivity. The best results related to diastereoselective reduction…