Enantioselectively functionalised phenytoin derivatives by auxiliary-directed N to C aryl migration in lithiated α-amino nitriles

Josep Mas-Roselló; Mary Okoh; Jonathan Clayden

doi:10.1039/c8cc06833j

Enantioselectively functionalised phenytoin derivatives by auxiliary-directed N to C aryl migration in lithiated α-amino nitriles

Josep Mas-Roselló, Mary Okoh, Jonathan Clayden^*

^*Corresponding author for this work

Research output: Contribution to journal › Article (Academic Journal) › peer-review

9 Citations (Scopus)

295 Downloads (Pure)

Abstract

Lithiation of N′-arylureas derived from amino nitriles incorporating a (1R,2R)-2-aminocyclohexanol chiral auxiliary leads to diastereoselective migration of the aryl ring to the position α to the nitrile. The resulting N′-lithiated ureas undergo spontaneous cyclisation to iminohydantoins, which may be hydrolysed to give chiral 5,5-diarylhydantoins related to phenytoin, in enantioenriched form.

Original language	English
Pages (from-to)	10985-10988
Number of pages	4
Journal	Chemical Communications
Volume	54
Issue number	78
Early online date	10 Sept 2018
DOIs	https://doi.org/10.1039/c8cc06833j
Publication status	Published - 7 Oct 2018

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Organic & Biological

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title = "Enantioselectively functionalised phenytoin derivatives by auxiliary-directed N to C aryl migration in lithiated α-amino nitriles",

abstract = "Lithiation of N′-arylureas derived from amino nitriles incorporating a (1R,2R)-2-aminocyclohexanol chiral auxiliary leads to diastereoselective migration of the aryl ring to the position α to the nitrile. The resulting N′-lithiated ureas undergo spontaneous cyclisation to iminohydantoins, which may be hydrolysed to give chiral 5,5-diarylhydantoins related to phenytoin, in enantioenriched form.",

author = "Josep Mas-Rosell{\'o} and Mary Okoh and Jonathan Clayden",

year = "2018",

month = oct,

day = "7",

doi = "10.1039/c8cc06833j",

language = "English",

volume = "54",

pages = "10985--10988",

journal = "Chemical Communications",

issn = "1359-7345",

publisher = "Royal Society of Chemistry",

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T1 - Enantioselectively functionalised phenytoin derivatives by auxiliary-directed N to C aryl migration in lithiated α-amino nitriles

AU - Mas-Roselló, Josep

AU - Okoh, Mary

AU - Clayden, Jonathan

PY - 2018/10/7

Y1 - 2018/10/7

N2 - Lithiation of N′-arylureas derived from amino nitriles incorporating a (1R,2R)-2-aminocyclohexanol chiral auxiliary leads to diastereoselective migration of the aryl ring to the position α to the nitrile. The resulting N′-lithiated ureas undergo spontaneous cyclisation to iminohydantoins, which may be hydrolysed to give chiral 5,5-diarylhydantoins related to phenytoin, in enantioenriched form.

AB - Lithiation of N′-arylureas derived from amino nitriles incorporating a (1R,2R)-2-aminocyclohexanol chiral auxiliary leads to diastereoselective migration of the aryl ring to the position α to the nitrile. The resulting N′-lithiated ureas undergo spontaneous cyclisation to iminohydantoins, which may be hydrolysed to give chiral 5,5-diarylhydantoins related to phenytoin, in enantioenriched form.

UR - https://www.scopus.com/pages/publications/85054151200

U2 - 10.1039/c8cc06833j

DO - 10.1039/c8cc06833j

M3 - Article (Academic Journal)

C2 - 30211399

AN - SCOPUS:85054151200

SN - 1359-7345

VL - 54

SP - 10985

EP - 10988

JO - Chemical Communications

JF - Chemical Communications

IS - 78

ER -

Enantioselectively functionalised phenytoin derivatives by auxiliary-directed N to C aryl migration in lithiated α-amino nitriles

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alpha-Arylation and alpha-Vinylation of Enolates: New Reactivity from the Urea Linkage.

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Enantioselectively functionalised phenytoin derivatives by auxiliary-directed N to C aryl migration in lithiated α-amino nitriles

Abstract

Research Groups and Themes

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alpha-Arylation and alpha-Vinylation of Enolates: New Reactivity from the Urea Linkage.

Cite this