Selective Construction of Quaternary Stereocentres in Radical Cyclisation Cascades triggered by electron-transfer reduction of amide-type carbonyls

Huanming Huang; Pablo Bonilla Dominguez; David Procter

doi:10.1039/C7OB00739F

Selective Construction of Quaternary Stereocentres in Radical Cyclisation Cascades triggered by electron-transfer reduction of amide-type carbonyls

Huanming Huang, Pablo Bonilla Dominguez, David Procter

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Abstract

Radical–radical cyclisation cascades, triggered by single-electron-transfer to amide-type carbonyls using SmI₂–H₂O–LiBr, result in the selective construction of quaternary carbon stereocentres. The cascades deliver tricyclic barbiturates with four stereocentres in good yield and with excellent diastereocontrol.

Original language	English
Pages (from-to)	4159-4164
Number of pages	6
Journal	Organic and Biomolecular Chemistry
Volume	15
Early online date	12 Apr 2017
DOIs	https://doi.org/10.1039/C7OB00739F
Publication status	Published - 2017

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DJP-HH-rev-article-OBC-Apr9Accepted author manuscript, 3.91 MB

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title = "Selective Construction of Quaternary Stereocentres in Radical Cyclisation Cascades triggered by electron-transfer reduction of amide-type carbonyls",

abstract = "Radical–radical cyclisation cascades, triggered by single-electron-transfer to amide-type carbonyls using SmI2–H2O–LiBr, result in the selective construction of quaternary carbon stereocentres. The cascades deliver tricyclic barbiturates with four stereocentres in good yield and with excellent diastereocontrol.",

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publisher = "Royal Society of Chemistry",

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AU - Huang, Huanming

AU - Bonilla Dominguez, Pablo

AU - Procter, David

PY - 2017

Y1 - 2017

N2 - Radical–radical cyclisation cascades, triggered by single-electron-transfer to amide-type carbonyls using SmI2–H2O–LiBr, result in the selective construction of quaternary carbon stereocentres. The cascades deliver tricyclic barbiturates with four stereocentres in good yield and with excellent diastereocontrol.

AB - Radical–radical cyclisation cascades, triggered by single-electron-transfer to amide-type carbonyls using SmI2–H2O–LiBr, result in the selective construction of quaternary carbon stereocentres. The cascades deliver tricyclic barbiturates with four stereocentres in good yield and with excellent diastereocontrol.

U2 - 10.1039/C7OB00739F

DO - 10.1039/C7OB00739F

M3 - Article

SN - 1477-0520

VL - 15

SP - 4159

EP - 4164

JO - Organic and Biomolecular Chemistry

JF - Organic and Biomolecular Chemistry

ER -

Selective Construction of Quaternary Stereocentres in Radical Cyclisation Cascades triggered by electron-transfer reduction of amide-type carbonyls

Abstract

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