Abstract
The copper(I) catalyzed alkyne-azide cycloaddition (CuAAC), a click reaction, is one of the most powerful catalytic reactions developed during the last two decades. Conducting CuAAC enantioselectively would add a third dimension to this reaction and would enable the direct synthesis of α-chiral triazoles. Doing so is demanding because the two precursors have linear geometries, and the triazole product is a flat heterocycle. Designing a chiral catalyst is further complicated by the complex mechanism of CuAAC. We report an enantioselective CuAAC (E-CuAAC), enabled by dynamic kinetic resolution (DKR). The E-CuAAC is high yielding and affords up to 99:1 er. The E-CuAAC can directly generate α-chiral triazoles in a complex molecular environment.
| Original language | English (US) |
|---|---|
| Pages (from-to) | 5135-5138 |
| Number of pages | 4 |
| Journal | Journal of the American Chemical Society |
| Volume | 141 |
| Issue number | 13 |
| DOIs | |
| State | Published - Apr 3 2019 |
Bibliographical note
Funding Information:We acknowledge the University of Minnesota and The American Chemical Society’s Petroleum Research Fund (PRF #56505-DNI1) for financial support. This research was supported by the National Institute of General Medical Sciences of the National Institutes of Health under Award No. R35GM124718.
Funding Information:
We acknowledge the University of Minnesota and The American Chemical Society???s Petroleum Research Fund (PRF #56505- DNI1) for financial support. This research was supported by the National Institute of General Medical Sciences of the National Institutes of Health under Award No. R35GM124718.
Publisher Copyright:
© 2019 American Chemical Society.