An Ylide Transformation of Rhodium(I) Carbene: Enantioselective Three-Component Reaction through Trapping of Rhodium(I)-Associated Ammonium Ylides by [beta]-Nitroacrylates

An Ylide Transformation of Rhodium(I) Carbene: Enantioselective Three-Component Reaction through Trapping of Rhodium(I)-Associated Ammonium Ylides by [beta]-Nitroacrylates

The chiral RhI-diene-catalyzed asymmetric three-component reaction of aryldiazoacetates, aromatic amines, and [beta]-nitroacrylates was achieved to obtain [gamma]-nitro-[alpha]-amino-succinates in good yields and with high diastereo- and enantioselectivity. This reaction is proposed to proceed throu...

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Veröffentlicht in:Angewandte Chemie International Edition 2014-11, Vol.53 (48), p.13136
Hauptverfasser: Ma, Xiaochu, Jiang, Jun, Lv, Siying, Yao, Wenfeng, Yang, Yang, Liu, Shunying, Xia, Fei, Hu, Wenhao
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Trapping
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container_issue 48
container_start_page 13136
container_title Angewandte Chemie International Edition
container_volume 53
creator Ma, Xiaochu
Jiang, Jun
Lv, Siying
Yao, Wenfeng
Yang, Yang
Liu, Shunying
Xia, Fei
Hu, Wenhao
description The chiral RhI-diene-catalyzed asymmetric three-component reaction of aryldiazoacetates, aromatic amines, and [beta]-nitroacrylates was achieved to obtain [gamma]-nitro-[alpha]-amino-succinates in good yields and with high diastereo- and enantioselectivity. This reaction is proposed to proceed through the enantioselective trapping of RhI-associated ammonium ylides by nitroacrylates. This new transformation represents the first example of RhI-carbene-induced ylide transformation.
doi_str_mv 10.1002/anie.201407740
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title An Ylide Transformation of Rhodium(I) Carbene: Enantioselective Three-Component Reaction through Trapping of Rhodium(I)-Associated Ammonium Ylides by [beta]-Nitroacrylates
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