Cooperative organocatalysis of Mukaiyama-type aldol reactions by thioureas and nitro compounds

Konstantin Bukhriakov; Victor G. Desyatkin; Valentin Rodionov

doi:10.1039/c6cc01984f

Cooperative organocatalysis of Mukaiyama-type aldol reactions by thioureas and nitro compounds

Konstantin Bukhriakov, Victor G. Desyatkin, Valentin Rodionov

Research output: Contribution to journal › Article › peer-review

11 Scopus citations

Abstract

A unique organocatalytic system for Mukaiyama-type aldol reactions based on the cooperative action of nitro compounds and thioureas has been identified. This system is compatible with a wide range of substrates and does not require low temperatures, inert atmospheres, or an aqueous workup. A catalytic mechanism based on nitro group-mediated silyl cation transfer has been proposed. © The Royal Society of Chemistry 2016.

Original language	English (US)
Pages (from-to)	7576-7579
Number of pages	4
Journal	Chem. Commun.
Volume	52
Issue number	48
DOIs	https://doi.org/10.1039/c6cc01984f
State	Published - 2016

Bibliographical note

KAUST Repository Item: Exported on 2020-10-01
Acknowledgements: This research was supported by King Abdullah University of Science and Technology (KAUST). We are grateful to Dr Xianrong Guo (KAUST) for his assistance with 29Si NMR, Dr Batian Chen (KAUST) for help with DFT calculations, and Sarah Almahdali (KAUST) for help with preparing the manuscript.

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title = "Cooperative organocatalysis of Mukaiyama-type aldol reactions by thioureas and nitro compounds",

abstract = "A unique organocatalytic system for Mukaiyama-type aldol reactions based on the cooperative action of nitro compounds and thioureas has been identified. This system is compatible with a wide range of substrates and does not require low temperatures, inert atmospheres, or an aqueous workup. A catalytic mechanism based on nitro group-mediated silyl cation transfer has been proposed. {\textcopyright} The Royal Society of Chemistry 2016.",

author = "Konstantin Bukhriakov and Desyatkin, {Victor G.} and Valentin Rodionov",

note = "KAUST Repository Item: Exported on 2020-10-01 Acknowledgements: This research was supported by King Abdullah University of Science and Technology (KAUST). We are grateful to Dr Xianrong Guo (KAUST) for his assistance with 29Si NMR, Dr Batian Chen (KAUST) for help with DFT calculations, and Sarah Almahdali (KAUST) for help with preparing the manuscript.",

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AU - Bukhriakov, Konstantin

AU - Desyatkin, Victor G.

AU - Rodionov, Valentin

N1 - KAUST Repository Item: Exported on 2020-10-01 Acknowledgements: This research was supported by King Abdullah University of Science and Technology (KAUST). We are grateful to Dr Xianrong Guo (KAUST) for his assistance with 29Si NMR, Dr Batian Chen (KAUST) for help with DFT calculations, and Sarah Almahdali (KAUST) for help with preparing the manuscript.

PY - 2016

Y1 - 2016

N2 - A unique organocatalytic system for Mukaiyama-type aldol reactions based on the cooperative action of nitro compounds and thioureas has been identified. This system is compatible with a wide range of substrates and does not require low temperatures, inert atmospheres, or an aqueous workup. A catalytic mechanism based on nitro group-mediated silyl cation transfer has been proposed. © The Royal Society of Chemistry 2016.

AB - A unique organocatalytic system for Mukaiyama-type aldol reactions based on the cooperative action of nitro compounds and thioureas has been identified. This system is compatible with a wide range of substrates and does not require low temperatures, inert atmospheres, or an aqueous workup. A catalytic mechanism based on nitro group-mediated silyl cation transfer has been proposed. © The Royal Society of Chemistry 2016.

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JO - Chem. Commun.

JF - Chem. Commun.

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ER -

Cooperative organocatalysis of Mukaiyama-type aldol reactions by thioureas and nitro compounds

Abstract

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