Details

Autor(en) / Beteiligte

• Brittain, William D. G.
• Dalling, Andrew G.
• Sun, Zhenquan
• Duff, Cécile S. Le
• Male, Louise
• Buckley, Benjamin R.
• Fossey, John S.

Titel

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

Ist Teil von

• Scientific reports, 2019-10, Vol.9 (1), p.15086-9, Article 15086

Ort / Verlag

London: Nature Publishing Group UK

Erscheinungsjahr

2019

Quelle

EZB Electronic Journals Library

Beschreibungen/Notizen

• A non-enzymatic simultaneous (coined coetaneous) kinetic resolution of a racemic alkyne and racemic azide, 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 diastereoisomer 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.