Candida antarctica lipase A - A powerful catalyst for the resolution of heteroaromatic β-amino esters
Enantioselective acylations of 3-amino-3-heteroarylpropanoates (ArCH(NH2)CH2CO2Et; Ar=2- or 3-thienyl or -furyl) were performed in the presence of Candida antarctica lipase A. As a result of the excellent chemo- and enantioselectivities (E >100), gram-scale resolutions were carried out in ethyl butanoate. The hydrochloride salts of the unreacted R substrates and the butanamides of the reactive S enantiomers were thus prepared.
Solymar, Magdolna,Fueloep, Ferenc,Kanerva, Liisa T.
p. 2383 - 2388
(2007/10/03)
Enantioselective β-amino acid synthesis based on catalyzed asymmetric acyl halide-aldehyde cyclocondensation reactions
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Nelson, Scott G.,Spencer, Keith L.
p. 1323 - 1325
(2007/10/03)
Electrogenerated chiral building blocks for diastereoselective amidoalkylation reactions
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.
Enantioselektive Synthese von β-Aminosaeuren - TMS-SAMP als chirales Ammoniak-Aequivalent in der azaanalogen Michael-Addition an α,β-ungesaettigte Ester