Synthesis 2019; 51(14): 2845-2864
DOI: 10.1055/s-0037-1611786
paper
© Georg Thieme Verlag Stuttgart · New York

Practical Synthesis of Chiral N-Heterocyclic Carbene Triazolium Salts Containing a Hydroxy Functional Handle

,
Kanchan Mal
,
Department of Chemistry, Ben-Gurion University of the Negev, Beer-Sheva 84105, Israel   Email: anatmilo@bgu.ac.il
› Author Affiliations
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.
Further Information

Publication History

Received: 04 February 2019

Accepted after revision: 19 March 2019

Publication Date:
02 April 2019 (eFirst)

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.

Supporting Information

 
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