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. 2015 Feb 1;6(2):1350-1354.
doi: 10.1039/c4sc03218g. Epub 2014 Nov 28.

Highly enantioselective access to diketopiperazines via cinchona alkaloid catalyzed Michael additions

Alejandro Cabanillas  1 , Christopher D Davies  2 , Louise Male  1 , Nigel S Simpkins  1
Affiliations

Highly enantioselective access to diketopiperazines via cinchona alkaloid catalyzed Michael additions

Alejandro Cabanillas et al. Chem Sci. .

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.

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Figures

Fig. 1
Fig. 1. Structures of significant bioactive DKPs.
Fig. 2
Fig. 2. The structure of one of the two crystallographically independent molecules of 6m, with ellipsoids drawn at the 50% probability level.
Fig. 3
Fig. 3. Model for 5d-catalyzed Michael addition leading to 6m.
Scheme 1
Scheme 1. Conversion of Michael adduct 6b into bridged DKP 8.
Scheme 2
Scheme 2. Regioselective reduction of TKP 6l to give DKP 10.
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