An Asymmetric Organocatalysis Approach to the Prenylated Alkaloid Family

Matt Rees; Nigel Simpkins; Louise Male

doi:10.1021/acs.orglett.7b00193

An Asymmetric Organocatalysis Approach to the Prenylated Alkaloid Family

Matt Rees, Nigel Simpkins, Louise Male

Chemistry

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6 Citations (Scopus)

282 Downloads (Pure)

Abstract

Michael addition of a proline-derived triketopiperazine (TKP) to β-substituted enones and acrylamides, mediated by a cinchona alkaloid catalyst, delivers products possessing a bicyclo[2.2.2]diazaoctane structure in high yield and enantiomeric ratio (er). Further modification of the amide products toward polycyclic scaffolds resembling members of the prenylated alkaloid
family is also demonstrated.

Original language	English
Pages (from-to)	1338-1341
Number of pages	4
Journal	Organic Letters
Early online date	23 Feb 2017
DOIs	https://doi.org/10.1021/acs.orglett.7b00193
Publication status	E-pub ahead of print - 23 Feb 2017

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SIMPKINS_organocatalysis_towards_prenylated_alkaloidsAccepted author manuscript, 402 KBLicence: None: All rights reserved

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abstract = "Michael addition of a proline-derived triketopiperazine (TKP) to β-substituted enones and acrylamides, mediated by a cinchona alkaloid catalyst, delivers products possessing a bicyclo[2.2.2]diazaoctane structure in high yield and enantiomeric ratio (er). Further modification of the amide products toward polycyclic scaffolds resembling members of the prenylated alkaloidfamily is also demonstrated.",

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AU - Male, Louise

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N2 - Michael addition of a proline-derived triketopiperazine (TKP) to β-substituted enones and acrylamides, mediated by a cinchona alkaloid catalyst, delivers products possessing a bicyclo[2.2.2]diazaoctane structure in high yield and enantiomeric ratio (er). Further modification of the amide products toward polycyclic scaffolds resembling members of the prenylated alkaloidfamily is also demonstrated.

AB - Michael addition of a proline-derived triketopiperazine (TKP) to β-substituted enones and acrylamides, mediated by a cinchona alkaloid catalyst, delivers products possessing a bicyclo[2.2.2]diazaoctane structure in high yield and enantiomeric ratio (er). Further modification of the amide products toward polycyclic scaffolds resembling members of the prenylated alkaloidfamily is also demonstrated.

U2 - 10.1021/acs.orglett.7b00193

DO - 10.1021/acs.orglett.7b00193

M3 - Article

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SP - 1338

EP - 1341

JO - Organic Letters

JF - Organic Letters

ER -

An Asymmetric Organocatalysis Approach to the Prenylated Alkaloid Family

Abstract

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