Highly enantioselective access to diketopiperazines via cinchona alkaloid catalyzed Michael additions

Alejandro Cabanillas; Christopher D. Davies; Louise Male; Nigel S. Simpkins

doi:10.1039/C4SC03218G

Highly enantioselective access to diketopiperazines via cinchona alkaloid catalyzed Michael additions

Alejandro Cabanillas, Christopher D. Davies, Louise Male, Nigel S. Simpkins

Chemistry

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14 Citations (Scopus)

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Abstract

Michael addition reactions of triketopiperazine (TKP) derivatives to enones, mediated by a cinchona alkaloid-derived catalyst, deliver products in high yield and enantiomeric ratio (er). Use of unsaturated ester, nitrile or sulfone partners gives bridged hydroxy-diketopiperazine (DKP) products resulting from a novel Michael addition–ring closure.

Original language	English
Journal	Chemical Science
Early online date	28 Nov 2014
DOIs	https://doi.org/10.1039/C4SC03218G
Publication status	Published - 2014

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10.1039/C4SC03218G

Cabanillas_et_al_Highly_enantioselective_access_Chemical_Science_2014
Eligibility for repository : checked 16/12/2014
Final published version, 267 KBLicence: Creative Commons: Attribution (CC BY)

http://xlink.rsc.org/?DOI=C4SC03218G

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title = "Highly enantioselective access to diketopiperazines via cinchona alkaloid catalyzed Michael additions",

abstract = "Michael addition reactions of triketopiperazine (TKP) derivatives to enones, mediated by a cinchona alkaloid-derived catalyst, deliver products in high yield and enantiomeric ratio (er). Use of unsaturated ester, nitrile or sulfone partners gives bridged hydroxy-diketopiperazine (DKP) products resulting from a novel Michael addition–ring closure.",

author = "Alejandro Cabanillas and Davies, {Christopher D.} and Louise Male and Simpkins, {Nigel S.}",

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journal = "Chemical Science",

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AU - Cabanillas, Alejandro

AU - Davies, Christopher D.

AU - Male, Louise

AU - Simpkins, Nigel S.

PY - 2014

Y1 - 2014

N2 - Michael addition reactions of triketopiperazine (TKP) derivatives to enones, mediated by a cinchona alkaloid-derived catalyst, deliver products in high yield and enantiomeric ratio (er). Use of unsaturated ester, nitrile or sulfone partners gives bridged hydroxy-diketopiperazine (DKP) products resulting from a novel Michael addition–ring closure.

AB - Michael addition reactions of triketopiperazine (TKP) derivatives to enones, mediated by a cinchona alkaloid-derived catalyst, deliver products in high yield and enantiomeric ratio (er). Use of unsaturated ester, nitrile or sulfone partners gives bridged hydroxy-diketopiperazine (DKP) products resulting from a novel Michael addition–ring closure.

U2 - 10.1039/C4SC03218G

DO - 10.1039/C4SC03218G

M3 - Article

SN - 2041-6520

JO - Chemical Science

JF - Chemical Science

ER -

Highly enantioselective access to diketopiperazines via cinchona alkaloid catalyzed Michael additions

Abstract

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