Enantioselective Alkyne-Mediated Aldehyde Allylation of Alcohol Proelectrophiles Using RuHCl(CO)(PPh <sub>3</sub> ) <sub>3</sub> as Precatalyst
The catalyst assembled from inexpensive RuHCl(CO)(PPh<sub>3</sub>)<sub>3</sub>, JOSIPHOS (SL-J009-1), and either NaI or KI affects <i>anti</i>-diastereo- and enantioselective alkyne-mediated allylation of alcohol proelectrophiles via hydrogen autotransfer. This protocol offers an alternative to the iodide-bound precatalyst RuI(CO)<sub>3</sub>(η<sup>3</sup>-C<sub>3</sub>H<sub>5</sub>), which is somewhat sensitive and not commercially available. Application to the asymmetric synthesis of <i>cis</i>-2,3-disubstituted pyrrolidines <b>5a</b>-<b>5c</b> and <i>cis</i>-2,3-disubstituted azetidine <b>6</b> is described.
Authors
- Madeline M. Evarts
- Michael J. Krische (ORCID: https://orcid.org/0000-0001-8418-9709)
- Tam Nguyen (ORCID: https://orcid.org/0009-0009-7358-8806)
Institutions
- The University of Texas at Austin (US)
Publication Details
- Journal
- Organic Letters
- Published
- 2025-12-18
- DOI
- https://doi.org/10.1021/acs.orglett.5c04678
- Primary Topic
- Asymmetric Hydrogenation and Catalysis
- Type
- article
- Field-Weighted Citation Impact
- 0.00