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Synthesis 2015; 47(15): 2199-2206
DOI: 10.1055/s-0034-1380718
DOI: 10.1055/s-0034-1380718
special topic
Primary Amine–2-Aminopyrimidine Chiral Organocatalysts for the Enantioselective Conjugate Addition of Branched Aldehydes to Maleimides
Further Information
Publication History
Received: 26 March 2015
Accepted after revision: 13 April 2015
Publication Date:
26 May 2015 (online)
Abstract
Chiral primary amines containing the (R,R)- and (S,S)-trans-cyclohexane-1,2-diamine scaffold and a pyrimidin-2-yl unit are synthesized and used as general organocatalysts for the Michael reaction of α-branched aldehydes to maleimides. The reaction takes place with 10 mol% organocatalyst loading and hexanedioic acid as cocatalyst in aqueous N,N-dimethylformamide at 10 °C affording the corresponding succinimides in good yields and enantioselectivities. DFT calculations support the stereochemical results and the role played by the solvents.
Supporting Information
- Supporting information for this article is available online at http://dx.doi.org/10.1055/s-0034-1380718.
- Supporting Information
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