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Synthesis 2019; 51(02): 463-469
DOI: 10.1055/s-0037-1610824
DOI: 10.1055/s-0037-1610824
paper
Asymmetric Synthesis of Adamantyl GABA Analogues
We gratefully acknowledge the financial support of the Russian Science Foundation, grant 18-13-00447.Further Information
Publication History
Received: 14 July 2018
Accepted after revision: 01 August 2018
Publication Date:
01 October 2018 (online)
Abstract
An efficient synthesis of (R)- and (S)-4-amino-3-(adamant-1-yl)butyric acids and (R)- and (S)-4-(adamant-1-yl)pyrrolidin-2-ones is presented. The synthetic strategy is based on asymmetric Michael addition of diethyl malonate to 1-(adamant-1-yl)-2-nitroethene using available Ni(II) complex as the catalyst. The procedures provide good to high enantioselectivity of Michael addition to sterically hindered nitroalkene and good yields of (R)- and (S)-enantiomers of 3-adamantyl substituted GABA.
Key words
Michael reaction - asymmetric synthesis - metal complex catalysis - chiral GABA analogues - optical rotation calculationsSupporting Information
- Supporting information for this article is available online at https://doi.org/10.1055/s-0037-1610824.
- Supporting Information
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