Enantioselective Butadiene-Mediated Aldehyde Crotylation of Alcohol Proelectrophiles: RuHCl(CO)(PPh <sub>3</sub> ) <sub>3</sub> as a Precatalyst
The catalyst assembled from inexpensive, air-stable RuHCl(CO)(PPh<sub>3</sub>)<sub>3,</sub> JOSIPHOS (SL-J502-1), and NaI affects <i>anti</i>-diastereo- and enantioselective crotylation of alcohol proelectrophiles via hydrogen autotransfer. This operationally simple protocol bypasses use of iodide-bearing precatalyst RuI(η<sup>3</sup>-C<sub>3</sub>H<sub>5</sub>)(CO)<sub>3</sub>, which is not commercially available. Using this method, formal syntheses of cryptophycins 1-4 and 24 are achieved in a fraction of the steps previously required.
Authors
- Catherine G. Santana (ORCID: https://orcid.org/0000-0001-8135-0149)
- P. Meares
- Michael J. Krische (ORCID: https://orcid.org/0000-0001-8418-9709)
- Dana E. Pfaffinger (ORCID: https://orcid.org/0000-0003-1668-0939)
Institutions
- The University of Texas at Austin (US)
Publication Details
- Journal
- Organic Letters
- Published
- 2025-12-26
- DOI
- https://doi.org/10.1021/acs.orglett.5c05046
- Citations
- 2
- Primary Topic
- Asymmetric Hydrogenation and Catalysis
- Type
- article
- Field-Weighted Citation Impact
- 1.07