183963-02-2Relevant academic research and scientific papers
Electrogenerated chiral 4-methoxy-2-oxazolidinones as diastereoselective amidoalkylation reagents for the synthesis of β-amino alcohol precursors
Schierle-Arndt, Kerstin,Kolter, Doris,Danielmeier, Karsten,Steckhan, Eberhard
, p. 2425 - 2433 (2007/10/03)
A flexible and efficient synthesis of enantiomerically pure 4,5-substituted 2-oxazolidinones - important target molecules as precursors of pharmacologically active 2-oxazolidinones, β-amino alcohols, β-blockers and azasugar derivatives - is described. As starting materials, the enantiopure storage forms of chiral N-acyliminium ions (4RS,5S)-5-chloromethyl-4-methoxy-1,3-oxazolidin-2-one (2) and (4RS,5R)-4-methoxy-5-methyl-1,3-oxazolidin-2-one (3) were used; these are readily available from the chiral pool with the aid of electrochemical transformations. Substitution of the 4-methoxy group in building blocks 2 and 3 with a large variety of organometallic nucleophiles resulted in the trans-diastereoselective formation of enantiopure 4,5-disubstituted 2-oxazolidinones, with a high degree of flexibility in the substituent at the 4-position.
Ein neues chirales, kationisches β-Aminoalkoholaequivalent: variabler Zugang zu enantiomerenreinen Bausteinen fuer Hydroxyethylendipeptid-Isostere
Danielmeier, Karsten,Schierle, Kerstin,Steckhan, Eberhard
, p. 2397 - 2399 (2007/10/03)
Keywords: Alkylierungen; Aminoalkohole; Epoxidierungen; Peptid-Isostere
Electrogenerated chiral building blocks for diastereoselective amidoalkylation reactions
Brungs,Danielmeier,Jakobi,Nothhelfer,Stahl,Zietlow,Steckhan
, p. 575 - 590 (2007/10/03)
Three different electrochemical methods have been applied for the synthesis of chiral building blocks for diastereoselective amidoalkylation reactions. These are A. the direct anodic α-methoxylation of amides and carbamates; B. anodic methoxylative decarboxylation of α-amino acid derivatives (Hofer-Moest reaction) C. indirect NaCl mediated anodic α-methoxylation of α-amino acid derivatives. The application of these building blocks for the synthesis of enantiomerically pure α-amino acids, dichiral 1,2-amino alcohols and chiral 1,3-diamines is described.
