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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.

SUBMITTER: Cabanillas A

PROVIDER: S-EPMC5811140 | biostudies-other | 2015 Feb

REPOSITORIES: biostudies-other

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Highly enantioselective access to diketopiperazines <i>via</i> cinchona alkaloid catalyzed Michael additions.

Cabanillas Alejandro A Davies Christopher D CD Male Louise L Simpkins Nigel S NS

Chemical science 20141128 2

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. ...[more]

PMID: 29560222

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