Homologation of α-amino acids to β-amino acids: 9-Fluorenylmethyl chloroformate as a carboxyl group activating agent for the synthesis of Nα-protected aminoacyldiazomethanes
An efficient and stereospecific homologation of urethane-protected α-amino acids to β-amino acids by Arndt-Eistert approach using an equimolar mixture of Fmoc-/Boc-/Z-α-amino acid and 9-fluorenylmethyl chloroformate for the acylation of diazomethane synth
Kantharaju,Suresh Babu, Vommina V.
p. 2152 - 2158
(2007/10/03)
Synthesis of Fmoc-β-homoamino acids by ultrasound-promoted wolff rearrangement
A highly efficient protocol for Amdt-Eistert chain elongation of the base-labile fluorenylmethoxycarbonyl (Fmoc) protected α-amino acids by Ag+- catalyzed, ultrasound-promoted Wolff rearrangement of the corresponding α- diazo ketones at room temperature is described. The enantiomeric purity of the products was examined by capillary zone electrophoresis with chiral buffer systems.
Müller, Annett,Vogt, Carla,Sewald, Norbert
p. 837 - 841
(2007/10/03)
Synthesis of N-{[(9H-Fluoren-9-yl)methoxy]carbonyl}-Protected (Fmoc) β-Amino Acids (= Homo-α-Amino Acids) by Direct Homologation
The successful application of the Arndt-Eistert protocol starting from commercially available N-{[(9H-fluoren-9-yl)methoxy]carbonyl}-protected (Fmoc) α-amino acids leading to enantiomerically pure N-Fmoc-Protected β-amino acids in only two steps and with high yield is reported.
Ellmerer-Mueller, Ernst P.,Broessner, Dagmar,Maslouh, Najib,Tako, Andreas
p. 59 - 65
(2007/10/03)
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