CuH‐Catalyzed Regio‐ and Enantioselective Hydroallylation of 1‐Trifluoromethylthioalkenes: Leaving Group–Dependent Stereochemistry
A copper-catalyzed regio- and enantioselective hydroallylation of 1-trifluoromethylthioalkenes with hydrosilanes and allylic electrophiles has been developed. The judicious choice of chiral ligands successfully promotes the enantioselective C(sp<sup>3</sup>)-C(sp<sup>3</sup>) bond formation at the α-position of trifluoromethylthio (SCF<sub>3</sub>) group, which is otherwise difficult to perform by other means. Experimental and computational mechanistic studies reveal that leaving groups of allylic electrophiles significantly influence the enantioselectivity as well as chemoselectivity.
Authors
- Satoshi Maeda (ORCID: https://orcid.org/0000-0001-8822-1147)
- Wataru Kanna (ORCID: https://orcid.org/0000-0002-2931-6661)
- Yuki Kojima (ORCID: https://orcid.org/0000-0002-3756-223X)
- Koji Hirano (ORCID: https://orcid.org/0000-0001-9752-1985)
- Yuji Nishii (ORCID: https://orcid.org/0000-0002-6824-0639)
- Shin‐ichi Suda
Institutions
- Hokkaido University of Science (JP)
- Hokkaido University (JP)
- The University of Osaka (JP)
Publication Details
- Journal
- Chemistry - A European Journal
- Published
- 2025-03-31
- DOI
- https://doi.org/10.1002/chem.202501210
- Citations
- 1
- Primary Topic
- Fluorine in Organic Chemistry
- Type
- article
- Field-Weighted Citation Impact
- 0.79