Enantioselective Synthesis of α-secondary and α-tertiary Piperazin-2-ones and Piperazines by Catalytic Asymmetric Allylic Alkylation

Overview

Journal Angew Chem Int Ed Engl

Specialty Chemistry

Date 2014 Nov 11

PMID 25382664

Citations 26

Authors

Katerina M Korch

Christian Eidamshaus

Douglas C Behenna

Sangkil Nam

David Horne

Brian M Stoltz

Affiliations

Soon will be listed here.

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.

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