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New efficient enantioselective synthesis of 2-oxopiperazines: a practical access to chiral 3-substituted 2-oxopiperazines

Authors
Publisher
Elsevier Ltd
Publication Date
Volume
19
Issue
14
Identifiers
DOI: 10.1016/j.tetasy.2008.06.030

Abstract

Abstract The development of efficient and stereoselective methods to produce 1,4-disubstituted-2-oxopiperazine in enantiomerically pure form, from a readily available starting material is crucial. Herein, we report a reduction modification to our previously described synthesis of 1,4-disubstituted-2-oxopiperazine and also two original shortly accessed pathways. These new pathways can be routinely performed on a multigram scale and should rapidly find a place in the preparation of the 3-substituted-2-oxopiperazine diastereomers. Stereoselective alkylation of 1,4-disubstituted-2-oxopiperazine led to the corresponding (3 S)-diastereomer or (3 R) -diastereomer from the corresponding 2-oxopiperazine enantiomer with the chiral inductor substituted at the N 1 (1 ∗) position, respectively, in good yield.

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