Journal
APPLIED CATALYSIS A-GENERAL
Volume 623, Issue -, Pages -Publisher
ELSEVIER
DOI: 10.1016/j.apcata.2021.118284
Keywords
Cyclic terpenes; Olefin metathesis; Ruthenium catalyst; Sustainable chemistry
Categories
Funding
- CAPES-COFECUB [88887.144564/2017-00]
- CNPq [312288/2019-0, 404843/2018-2]
- FAPESP [2018/01258-5, 2017/24931-4, 2016/05006-5, BEPE 2019/18981-4, 2015/26787-2]
- CAPES [001]
- CAPES-COFECUB (France) [PHC 884-17]
- CAPES-COFECUB (Brazil) [883/2017]
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The direct functionalization of sterically demanding alpha,alpha-disubstituted double bonds in beta-pinene, (-)-limonene and (-)-limonene terpenoids has been achieved through cross metathesis with internal olefins. This clean transformation provides a new method for accessing functionalized bulky cyclic terpenes, where the terminal double bond generates a trisubstituted olefin.
The straightforward functionalization of sterically demanding alpha,alpha-disubstituted double bonds of beta-pinene, (-)-limonene and (-)-limonene terpenoids has been achieved via cross metathesis with internal olefins. The reactions are catalyzed by second generation ruthenium catalysts in dimethyl carbonate as green solvent or under neat conditions. This transformation provides a clean process for the access to functionalized bulky cyclic terpenes where the terminal double bond generates a trisubstituted olefin.
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