Asymmetric counteranion-directed Lewis acid organocatalysis for the scalable cyanosilylation of aldehydes

Asymmetric counteranion-directed Lewis acid organocatalysis for the scalable cyanosilylation of aldehydes

Asymmetric cyanosilyation is a powerful method to convert carbonyls to chiral, configurationally stable cyanohydrins. Here, the authors report a catalyst capable of carrying out this reaction on large scales with extremely low catalyst loading, and also identify and explain a dormant period in the c...

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Main Authors: Zhipeng Zhang, Han Yong Bae, Joyram Guin, Constantinos Rabalakos, Manuel van Gemmeren, Markus Leutzsch, Martin Klussmann, Benjamin List
Format: Article
Language:English
Published: Nature Publishing Group 2016-08-01
Series:Nature Communications
Online Access:https://doi.org/10.1038/ncomms12478
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spelling doaj-14c5c2fe915f4d278e64b0b1946afdfa2021-05-11T11:10:14ZengNature Publishing GroupNature Communications2041-17232016-08-01711810.1038/ncomms12478Asymmetric counteranion-directed Lewis acid organocatalysis for the scalable cyanosilylation of aldehydesZhipeng Zhang0Han Yong Bae1Joyram Guin2Constantinos Rabalakos3Manuel van Gemmeren4Markus Leutzsch5Martin Klussmann6Benjamin List7Max-Planck-Institut für KohlenforschungMax-Planck-Institut für KohlenforschungMax-Planck-Institut für KohlenforschungMax-Planck-Institut für KohlenforschungMax-Planck-Institut für KohlenforschungMax-Planck-Institut für KohlenforschungMax-Planck-Institut für KohlenforschungMax-Planck-Institut für KohlenforschungAsymmetric cyanosilyation is a powerful method to convert carbonyls to chiral, configurationally stable cyanohydrins. Here, the authors report a catalyst capable of carrying out this reaction on large scales with extremely low catalyst loading, and also identify and explain a dormant period in the cycle.https://doi.org/10.1038/ncomms12478
collection DOAJ
language English
format Article
sources DOAJ
author Zhipeng Zhang
Han Yong Bae
Joyram Guin
Constantinos Rabalakos
Manuel van Gemmeren
Markus Leutzsch
Martin Klussmann
Benjamin List
spellingShingle Zhipeng Zhang
Han Yong Bae
Joyram Guin
Constantinos Rabalakos
Manuel van Gemmeren
Markus Leutzsch
Martin Klussmann
Benjamin List
Asymmetric counteranion-directed Lewis acid organocatalysis for the scalable cyanosilylation of aldehydes
Nature Communications
author_facet Zhipeng Zhang
Han Yong Bae
Joyram Guin
Constantinos Rabalakos
Manuel van Gemmeren
Markus Leutzsch
Martin Klussmann
Benjamin List
author_sort Zhipeng Zhang
title Asymmetric counteranion-directed Lewis acid organocatalysis for the scalable cyanosilylation of aldehydes
title_short Asymmetric counteranion-directed Lewis acid organocatalysis for the scalable cyanosilylation of aldehydes
title_full Asymmetric counteranion-directed Lewis acid organocatalysis for the scalable cyanosilylation of aldehydes
title_fullStr Asymmetric counteranion-directed Lewis acid organocatalysis for the scalable cyanosilylation of aldehydes
title_full_unstemmed Asymmetric counteranion-directed Lewis acid organocatalysis for the scalable cyanosilylation of aldehydes
title_sort asymmetric counteranion-directed lewis acid organocatalysis for the scalable cyanosilylation of aldehydes
publisher Nature Publishing Group
series Nature Communications
issn 2041-1723
publishDate 2016-08-01
description Asymmetric cyanosilyation is a powerful method to convert carbonyls to chiral, configurationally stable cyanohydrins. Here, the authors report a catalyst capable of carrying out this reaction on large scales with extremely low catalyst loading, and also identify and explain a dormant period in the cycle.
url https://doi.org/10.1038/ncomms12478
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AT hanyongbae asymmetriccounteraniondirectedlewisacidorganocatalysisforthescalablecyanosilylationofaldehydes
AT joyramguin asymmetriccounteraniondirectedlewisacidorganocatalysisforthescalablecyanosilylationofaldehydes
AT constantinosrabalakos asymmetriccounteraniondirectedlewisacidorganocatalysisforthescalablecyanosilylationofaldehydes
AT manuelvangemmeren asymmetriccounteraniondirectedlewisacidorganocatalysisforthescalablecyanosilylationofaldehydes
AT markusleutzsch asymmetriccounteraniondirectedlewisacidorganocatalysisforthescalablecyanosilylationofaldehydes
AT martinklussmann asymmetriccounteraniondirectedlewisacidorganocatalysisforthescalablecyanosilylationofaldehydes
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