Synthesis of α-Boryl-α-Substituted Allylboronates from Propyne
A novel method for the two-step synthesis of α-boryl-α-substituted allylboronates from propyne is described. These allylboronates are prepared by the Co-catalyzed 1,1-diboration reaction of propyne with B<sub>2</sub>pin<sub>2</sub>, followed by the base-mediated alkylation reaction of 1,1-di(boryl)propene at the α-position. Computational studies revealed the origins of observed reactivity and selectivity in the base-mediated alkylation reaction. The resulting α-boryl-α-methyl-allylboronate is applied to the allylation of aldehydes, which gives homoallylic alcohols with a trisubstituted alkene moiety.
Authors
- Ken Yamazaki (ORCID: https://orcid.org/0000-0002-2039-4321)
- Tomoya Miura (ORCID: https://orcid.org/0000-0003-2493-0184)
- Naoki Oku (ORCID: https://orcid.org/0009-0009-5847-9943)
- Hideko Takayanagi (ORCID: https://orcid.org/0000-0003-3212-9506)
Institutions
- Okayama University (JP)
- Kyoto University (JP)
- Kyoto Katsura Hospital (JP)
Publication Details
- Journal
- Organic Letters
- Published
- 2024-11-13
- DOI
- https://doi.org/10.1021/acs.orglett.4c03683
- Citations
- 1
- Primary Topic
- Organoboron and organosilicon chemistry
- Type
- article
- Field-Weighted Citation Impact
- 0.25
Funders
- Japan Science and Technology Corporation
- Astellas Foundation for Research on Metabolic Disorders
- Japan Society for the Promotion of Science