ChemRxiv
These are preliminary reports that have not been peer-reviewed. They should not be regarded as conclusive, guide clinical practice/health-related behavior, or be reported in news media as established information. For more information, please see our FAQs.
1/1
6 files

Simultaneous Clicknetic Resolution Coetaneous catalytic kinetic resolution of alkynes and azides through asymmetric triazole formation

preprint
submitted on 04.12.2017, 18:38 and posted on 05.12.2017, 17:10 by William D. G. Brittain, Andrew G. Dalling, Zhenquan Sun, Cecile S. Le Duff, Louise Male, Benjamin R. Buckley, John Fossey
A non-enzymatic simultaneous kinetic resolution of racemic alkynes and racemic azides utilising an asymmetric CuAAC reaction is reported. The use of a CuCl (R,R)Ph-Pybox catalyst system effects a simultaneous kinetic resolution of two racemic starting materials to give one major triazolic diasteroisomer in the ratio 74:12:4:10 (dr 84:16, 90% ee maj). The corresponding control reaction using an achiral copper catalyst gives the four possible diastereoisomers in a 23:27:23:27 ratio, demonstrating minimal inherent substrate control.

Funding

RCUK, Royal Society, EPSRC (EP/J003220/1), Wellcome Trust ISSF, University of Birmingham, Loughborough University

History

Topic

  • Homogeneous Catalysis

Email Address of Submitting Author

j.s.fossey@bham.ac.uk

Email Address(es) for Other Author(s)

wdb996@bham.ac.uk ad16973@bristol.ac.uk sunzhq3@mail2.sysu.edu.cn c.s.leduff@bham.ac.uk L.Male@bham.ac.uk B.R.Buckley@lboro.ac.uk

Institution

University of Birmingham

Country

United Kingdom

ORCID For Submitting Author

0000-0002-2626-5117

Declaration of Conflict of Interest

No conflict of interest

Exports