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DOI: 10.1055/s-0037-1611786
Practical Synthesis of Chiral N-Heterocyclic Carbene Triazolium Salts Containing a Hydroxy Functional Handle
This work was supported by the Israel Science Foundation (Grant No. 14-50-00126). V.D. gratefully acknowledges the Israeli Council for Higher Education's Planning and Budgeting Committee (PBC) for a postdoctoral fellowship. K.M. gratefully acknowledges the Kreitman Graduate School for a postdoctoral fellowship.Publication History
Received: 04 February 2019
Accepted after revision: 19 March 2019
Publication Date:
02 April 2019 (online)
Published as part of the Bürgenstock Special Section 2018 Future Stars in Organic Chemistry
Abstract
A library of functionalized chiral pyrrolidine-based N-heterocyclic carbene triazolium salts containing a hydroxy handle is prepared from readily accessible chiral (S)-pyroglutamic acid in eight steps. This improved synthetic protocol affords increased yields for known structures and 18 new NHCs are prepared by this method. The presence of a hydroxy handle offers potential for further functionalization and for non-covalent control over catalytic reactions in which the NHCs can serve as organocatalysts or ligands for organometallic catalysis.
Key words
N-heterocyclic carbenes - triazolium salts - organocatalysis - organomagnesium reagents - arylhydrazines - benzyl alcohol - protecting groups - desilylationSupporting Information
- Supporting information for this article is available online at https://doi.org/10.1055/s-0037-1611786.
- Supporting Information
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