Synthesis of a chiral quaternary carbon center bearing a fluorine atom: Enantio- and diastereoselective guanidine-catalyzed addition of fluorocarbon nucleophiles

Please use this identifier to cite or link to this item: https://doi.org/10.1002/anie.200900964

Title:	Synthesis of a chiral quaternary carbon center bearing a fluorine atom: Enantio- and diastereoselective guanidine-catalyzed addition of fluorocarbon nucleophiles
Authors:	Jiang, Z. Pan, Y. Zhao, Y. Ma, T. Lee, R. Yang, Y. Huang, K.-W. Wong, M.W. Tan, C.-H.
Keywords:	Asymmetric catalysis Fluorine Guanidine Michael addition Transition states
Issue Date:	4-May-2009
Citation:	Jiang, Z., Pan, Y., Zhao, Y., Ma, T., Lee, R., Yang, Y., Huang, K.-W., Wong, M.W., Tan, C.-H. (2009-05-04). Synthesis of a chiral quaternary carbon center bearing a fluorine atom: Enantio- and diastereoselective guanidine-catalyzed addition of fluorocarbon nucleophiles. Angewandte Chemie - International Edition 48 (20) : 3627-3631. ScholarBank@NUS Repository. https://doi.org/10.1002/anie.200900964
Abstract:	The perfect combination: The title reaction provides adducts having quaternary carbon centers bearing a fluorine atom with high ee and d.r. values (see scheme). The mechanism and origin of stereoselectivity were elucidated by DFT calculations. The bifunctional mode of the guanidine catalysis was demonstrated in the transition states resulting from the DFT results. © 2009 Wiley-VCH Verlag GmbH & Co. KGaA.
Source Title:	Angewandte Chemie - International Edition
URI:	http://scholarbank.nus.edu.sg/handle/10635/77172
ISSN:	14337851
DOI:	10.1002/anie.200900964
Appears in Collections:	Staff Publications

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