Please use this identifier to cite or link to this item:
https://doi.org/10.1002/chem.201100687
Title: | Expanding the utility of Brønsted base catalysis: Biomimetic enantioselective decarboxylative reactions | Authors: | Pan, Y. Kee, C.W. Jiang, Z. Ma, T. Zhao, Y. Yang, Y. Xue, H. Tan, C.-H. |
Keywords: | amination biomimetic synthesis decarboxylation density functional calculations Mannich reaction organocatalysis |
Issue Date: | 18-Jul-2011 | Citation: | Pan, Y., Kee, C.W., Jiang, Z., Ma, T., Zhao, Y., Yang, Y., Xue, H., Tan, C.-H. (2011-07-18). Expanding the utility of Brønsted base catalysis: Biomimetic enantioselective decarboxylative reactions. Chemistry - A European Journal 17 (30) : 8363-8370. ScholarBank@NUS Repository. https://doi.org/10.1002/chem.201100687 | Abstract: | As a result of the low reactivity of simple esters, the use of them as nucleophiles in direct asymmetric transformations is a long-standing challenge in synthetic organic chemistry. Nature approaches this difficulty through a decarboxylative mechanism, which is used for polyketide synthesis. Inspired by nature, we report guanidine-catalyzed biomimetic decarboxylative C-C and C-N bond-formation reactions. These highly enantioselective decarboxylative Mannich and amination reactions utilized malonic acid half thioesters as simple ester surrogates. It is proposed that nucleophilic addition precedes decarboxylation in the mechanism, which has been investigated in detail through the identification of intermediates by using electrospray ionization (ESI) mass-spectrometric analysis and DFT calculations. Copyright © 2011 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim. | Source Title: | Chemistry - A European Journal | URI: | http://scholarbank.nus.edu.sg/handle/10635/76152 | ISSN: | 09476539 | DOI: | 10.1002/chem.201100687 |
Appears in Collections: | Staff Publications |
Show full item record
Files in This Item:
There are no files associated with this item.
Items in DSpace are protected by copyright, with all rights reserved, unless otherwise indicated.