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- Title
NaOH/BEt<sub>3</sub> Catalyzed Regioselective Hydroboration of Epoxides to Secondary Alcohols.
- Authors
Wang, Jiali; Yao, Wubin; Hu, Dandan; Qi, Xinxin; Zhang, Jun‐Qi; Ren, Hongjun
- Abstract
A regioselective hydroboration/hydrolysis of epoxides with pinacolborane catalyzed by NaOH/BEt3 was achieved. Glycidyl oxide, styrene oxide and adamantane epoxide underwent facile hydroboration/deprotection to provide secondary alcohols with exclusive selectivity in good to excellent yields. Moreover, the stereochemistry of epoxides could also be well retained, and the corresponding secondary alcohols were obtained with high optical activity under alkaline catalysis. Significantly, in this reaction, diverse functional groups can be compatible, including hydrogenation‐sensitive groups, such as carbon‐carbon double bonds and halogens.
- Subjects
EPOXY compounds; HYDROBORATION; ALCOHOL; OPTICAL rotation; CARBON-carbon bonds; STYRENE oxide; ALCOHOL oxidation; HYDROLYSIS
- Publication
European Journal of Organic Chemistry, 2022, Vol 2022, Issue 35, p1
- ISSN
1434-193X
- Publication type
Article
- DOI
10.1002/ejoc.202200759