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|Title:||Phosphine-catalyzed enantioselective γ-addition of 3-substituted oxindoles to 2,3-butadienoates and 2-butynoates: Use of prochiral nucleophiles|
quaternary carbon centers
|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|
|Appears in Collections:||Staff Publications|
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