Please use this identifier to cite or link to this item: http://scholarbank.nus.edu.sg/handle/10635/93782
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.
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/10635/93782
ISSN: 09476539
Appears in Collections:Staff Publications

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