Core-Structure-Oriented Asymmetric Organocatalytic Substitution of 3-Hydroxyoxindoles: Application in the Enantioselective Total Synthesis of (+)-Folicanthine

Something constructive: The title reaction involving 3‐hydroxyoxindoles gives 3,3′‐disubstituted oxindoles with concomitant generation of an all‐carbon quaternary stereogenic center in high yield and excellent enantioselectivity. This reaction enabled the enantioselective construction of hexahydropy...

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Veröffentlicht in:Angewandte Chemie International Edition 2012-01, Vol.51 (4), p.1046-1050
Hauptverfasser: Guo, Chang, Song, Jin, Huang, Jian-Zhou, Chen, Peng-Hao, Luo, Shi-Wei, Gong, Liu-Zhu
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container_issue 4
container_start_page 1046
container_title Angewandte Chemie International Edition
container_volume 51
creator Guo, Chang
Song, Jin
Huang, Jian-Zhou
Chen, Peng-Hao
Luo, Shi-Wei
Gong, Liu-Zhu
description Something constructive: The title reaction involving 3‐hydroxyoxindoles gives 3,3′‐disubstituted oxindoles with concomitant generation of an all‐carbon quaternary stereogenic center in high yield and excellent enantioselectivity. This reaction enabled the enantioselective construction of hexahydropyrroloindole skeletons and the first catalytic enantioselective total synthesis of (+)‐folicanthine.
doi_str_mv 10.1002/anie.201107079
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subjects alkaloids
asymmetric catalysis
Brønsted acids
Carbamates - chemistry
Catalysis
Indoles - chemical synthesis
Indoles - chemistry
organocatalysis
Phosphoric Acids - chemistry
Pyrroles - chemical synthesis
Pyrroles - chemistry
Stereoisomerism
total synthesis
title Core-Structure-Oriented Asymmetric Organocatalytic Substitution of 3-Hydroxyoxindoles: Application in the Enantioselective Total Synthesis of (+)-Folicanthine
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