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https://doi.org/10.1002/anie.201307757
Title: | Phosphine-catalyzed enantioselective γ-addition of 3-substituted oxindoles to 2,3-butadienoates and 2-butynoates: Use of prochiral nucleophiles | Authors: | Wang, T. Yao, W. Zhong, F. Pang, G.H. Lu, Y. |
Keywords: | γ-addition allylation bifunctional phosphines oxindoles quaternary carbon centers |
Issue Date: | 10-Mar-2014 | Citation: | Wang, T., Yao, W., Zhong, F., Pang, G.H., Lu, Y. (2014-03-10). Phosphine-catalyzed enantioselective γ-addition of 3-substituted oxindoles to 2,3-butadienoates and 2-butynoates: Use of prochiral nucleophiles. Angewandte Chemie - International Edition 53 (11) : 2964-2968. ScholarBank@NUS Repository. https://doi.org/10.1002/anie.201307757 | Abstract: | The first phosphine-catalyzed enantioselective γ-addition with prochiral nucleophiles and 2,3-butadienoates as the reaction partners has been developed. Both 3-alkyl- and 3-aryl-substituted oxindoles could be employed in this process, which is catalyzed by a chiral phosphine that is derived from an amino acid, thus affording oxindoles that bear an all-carbon quaternary center at the 3-position in high yields and excellent enantioselectivity. The synthetic value of these γ-addition products was demonstrated by the formal total synthesis of two natural products and by the preparation of biologically relevant molecules and structural scaffolds. © 2014 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim. | Source Title: | Angewandte Chemie - International Edition | URI: | http://scholarbank.nus.edu.sg/handle/10635/94509 | ISSN: | 14337851 | DOI: | 10.1002/anie.201307757 |
Appears in Collections: | Staff Publications |
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