Please use this identifier to cite or link to this item: 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
Source: 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
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