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Enantioselective synthesis of ?-secondary and ?-tertiary piperazin-2-ones and piperazines by catalytic asymmetric allylic alkylation.

ABSTRACT: The asymmetric palladium-catalyzed decarboxylative allylic alkylation of differentially N-protected piperazin-2-ones allows the synthesis of a variety of highly enantioenriched tertiary piperazine-2-ones. Deprotection and reduction affords the corresponding tertiary piperazines, which can be employed for the synthesis of medicinally important analogues. The introduction of these chiral tertiary piperazines resulted in imatinib analogues which exhibited comparable antiproliferative activity to that of their corresponding imatinib counterparts.

SUBMITTER: Korch KM 

PROVIDER: S-EPMC4285707 | biostudies-literature | 2015 Jan

REPOSITORIES: biostudies-literature

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Enantioselective synthesis of α-secondary and α-tertiary piperazin-2-ones and piperazines by catalytic asymmetric allylic alkylation.

Korch Katerina M KM   Eidamshaus Christian C   Behenna Douglas C DC   Nam Sangkil S   Horne David D   Stoltz Brian M BM  

Angewandte Chemie (International ed. in English) 20141107 1

The asymmetric palladium-catalyzed decarboxylative allylic alkylation of differentially N-protected piperazin-2-ones allows the synthesis of a variety of highly enantioenriched tertiary piperazine-2-ones. Deprotection and reduction affords the corresponding tertiary piperazines, which can be employed for the synthesis of medicinally important analogues. The introduction of these chiral tertiary piperazines resulted in imatinib analogues which exhibited comparable antiproliferative activity to th  ...[more]

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