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Type: Artigo de periódico
Title: Synthesis of conformationally restricted acetylcholine analogues. Comparing lipase-mediated resolution with simulated moving bed chromatography of arylated beta-hydroxy-pyrrolidines
Author: Barreto, RD
Carpes, MJS
Santana, CC
Correia, CRD
Abstract: The enantiodivergent synthesis of new, conformationally restricted acetylcholine analogues was accomplished using arylated endocyclic enecarbamates as key intermediates. Stereoselective hydroboration of the aryl enecarbamates provided the corresponding aryl-ss-hydroxy-pyrrolidines. Acetylation, deprotection, followed by N-bismethylation, led to the desired betaine products. The kinetic resolution of the intermediate alcohols was performed by lipase-mediated hydrolysis of its acetate derivatives, resulting in excellent enantioselectivities (E > 100). An enzymatic enantiopreference predicted by the Kazlauskas's model was confirmed following Riguera's protocol. Finally, chromatographic resolution of racemic alcohol 5a was evaluated by semi-preparative scale chiral simulated moving bed chromatography and its performance compared with biocatalysis. (c) 2007 Elsevier Ltd. All rights reserved.
Country: Inglaterra
Editor: Pergamon-elsevier Science Ltd
Citation: Tetrahedron-asymmetry. Pergamon-elsevier Science Ltd, v. 18, n. 3, n. 435, n. 442, 2007.
Rights: fechado
Identifier DOI: 10.1016/j.tetasy.2007.01.030
Date Issue: 2007
Appears in Collections:Unicamp - Artigos e Outros Documentos

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