Please use this identifier to cite or link to this item: https://doi.org/10.1002/chem.200902830
Title: Enantioselective synthesis of α-fluorinated β-amino acid derivatives by an asymmetric mannich reaction and selective deacylation/ decarboxylation reactions
Authors: Pan, Y.
Zhao, Y. 
Ma, T.
Yang, Y.
Liu, H.
Jiang, Z.
Tan, C.-H. 
Keywords: Decarboxylation
Fluorocarbon nucleophiles
Guanidine
Mannich reaction
Retro-Claisen condensation
Issue Date: 18-Jan-2010
Source: Pan, Y., Zhao, Y., Ma, T., Yang, Y., Liu, H., Jiang, Z., Tan, C.-H. (2010-01-18). Enantioselective synthesis of α-fluorinated β-amino acid derivatives by an asymmetric mannich reaction and selective deacylation/ decarboxylation reactions. Chemistry - A European Journal 16 (3) : 779-782. ScholarBank@NUS Repository. https://doi.org/10.1002/chem.200902830
Abstract: A study was conducted to demonstrate enantioselective synthesis of α-fluorinated β-amino acid (AA) derivatives by an asymmetric Mannich reaction and selective deacylation or decarboxylation reactions. Better yield was obtained from the Mannich reaction between α-fluoro-β-ketoester and N-ethoxycarbonyl imine under the preliminary studies. The performance of β-keto acetyloxazolidinone was evaluated with a series of different N-Eoc imines in the presence of 10 mol% of bicyclic guanidine catalyst after establishing optimized conditions. Better results were observed with imines containing both electron-withdrawing and electron-donating aryl groups. The study focused on preparing α-fluoro-β-sulfones to determine their potential for the reaction. The Mannich reaction of 1-fluoro-1-(phenylsulfonyl) propan-2-α-fluoro-β-sulfones gave an adduct with a high ee value and good diastereoselectivity.
Source Title: Chemistry - A European Journal
URI: http://scholarbank.nus.edu.sg/handle/10635/76112
ISSN: 09476539
DOI: 10.1002/chem.200902830
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