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|Title:||Stereoselective synthesis of azetidine-derived glutamate and aspartate analogues from chiral azetidin-3-ones|
|Author:||Burtoloso, Antonio Carlos B.|
Correia, Carlos Roque D.
|Abstract:||The stereoselective syntheses of cis conformationally constrained glutamate and aspartate analogues, containing an azetidine framework were accomplished from (S)-N-tosyl-2-phenylglycine in moderate overall yields. The key steps in these syntheses involved an efficient Wittig olefination of an azetidin-3-one, followed by a highly stereoselective rhodium catalyzed hydrogenation. The route could also be applied to the synthesis of a trans glutamate analogue, since epimerization of cis to trans isomer could be performed using DBU in toluene at reflux|
|Appears in Collections:||IQ - Artigos e Outros Documentos|
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