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

preprint
submitted on 04.12.2017 and posted on 05.12.2017 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

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