Please use this identifier to cite or link to this item:
https://doi.org/10.1002/chem.200902830
DC Field | Value | |
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dc.title | Enantioselective synthesis of α-fluorinated β-amino acid derivatives by an asymmetric mannich reaction and selective deacylation/ decarboxylation reactions | |
dc.contributor.author | Pan, Y. | |
dc.contributor.author | Zhao, Y. | |
dc.contributor.author | Ma, T. | |
dc.contributor.author | Yang, Y. | |
dc.contributor.author | Liu, H. | |
dc.contributor.author | Jiang, Z. | |
dc.contributor.author | Tan, C.-H. | |
dc.date.accessioned | 2014-06-23T05:38:43Z | |
dc.date.available | 2014-06-23T05:38:43Z | |
dc.date.issued | 2010-01-18 | |
dc.identifier.citation | 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 | |
dc.identifier.issn | 09476539 | |
dc.identifier.uri | http://scholarbank.nus.edu.sg/handle/10635/76112 | |
dc.description.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. | |
dc.description.uri | http://libproxy1.nus.edu.sg/login?url=http://dx.doi.org/10.1002/chem.200902830 | |
dc.source | Scopus | |
dc.subject | Decarboxylation | |
dc.subject | Fluorocarbon nucleophiles | |
dc.subject | Guanidine | |
dc.subject | Mannich reaction | |
dc.subject | Retro-Claisen condensation | |
dc.type | Article | |
dc.contributor.department | CHEMISTRY | |
dc.description.doi | 10.1002/chem.200902830 | |
dc.description.sourcetitle | Chemistry - A European Journal | |
dc.description.volume | 16 | |
dc.description.issue | 3 | |
dc.description.page | 779-782 | |
dc.description.coden | CEUJE | |
dc.identifier.isiut | 000274615700008 | |
Appears in Collections: | Staff Publications |
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