( <i>E</i> )-Selective Weinreb Amide-Type Horner–Wadsworth–Emmons Reaction: Effect of Reaction Conditions, Substrate Scope, Isolation of a Reactive Magnesium Phosphonoenolate, and Applications
An <sup><i>i</i></sup>PrMgCl-deprotonating Weinreb amide-type Horner-Wadsworth-Emmons (HWE) reaction was developed, and the effects of diverse reaction conditions, including the base, cation, solvent, and concentration, were investigated to broaden the substrate scope and achieve high (<i>E</i>)-selectivity. The Weinreb amide-type phosphonoenolate generated from <sup><i>i</i></sup>PrMgCl was found to be isolable, stable for at least over a half year, and applicable in the HWE reaction keeping high productivity and selectivity compared with the in situ generated phosphonoenolate. The results prompted us to perform an application study including successive elongation, synthesis of a biscyclopropane, and Weinreb ketone syntheses.
Authors
- Hisazumi Tsutsui (ORCID: https://orcid.org/0009-0009-2371-8035)
- Isamu Shiina (ORCID: https://orcid.org/0000-0002-8749-2540)
- Takatsugu Murata (ORCID: https://orcid.org/0000-0002-3933-8928)
Institutions
- Tokyo University of Science (JP)
Publication Details
- Journal
- The Journal of Organic Chemistry
- Published
- 2024-10-11
- DOI
- https://doi.org/10.1021/acs.joc.4c01140
- Citations
- 7
- Primary Topic
- Phosphorus compounds and reactions
- Type
- article
- Field-Weighted Citation Impact
- 1.75
Funders
- Suntory Foundation for Life Sciences
- Japan Science and Technology Corporation
- Suntory Foundation