Functionalization of (-)-beta-pinene and (-)-limonene via cross metathesis with symmetrical internal olefins

Author(s)

Fernandes, Luciana Sarmento ^{[1, 2]} ; Mandelli, Dalmo ^[1] ; Carvalho, Wagner A. ^[1] ; Fischmeister, Cedric ^[2] ; Bruneau, Christian ^[2]

Affiliation

^[1] Univ Fed ABC, Ctr Ciencias Nat & Humanas, Santo Andre, SP - Brazil

^[2] Univ Rennes, ISCR, CNRS, UMR6226, F-35000 Rennes - France

• Document type: Journal article
• Source: Catalysis Communications; v. 135, FEB 2020.
• Web of Science Citations: 1

Abstract

The straightforward functionalization of sterically demanding alpha,alpha-disubstituted double bonds of the natural products beta-pinene and limonene via cross metathesis with symmetrical internal olefins is described. The reaction is catalyzed by Hoveyda-Grubbs type ruthenium catalysts in dimethyl carbonate as green solvent and makes possible the clean introduction of ester and nitrile groups in one step without formation of byproducts. (AU)

• FAPESP's process: 15/26787-2 - Valuation of natural products via cross-methathesis of terpenes and terpenoids
• Grantee: Luciana Sarmento Fernandes
• Support Opportunities: Scholarships in Brazil - Doctorate
• FAPESP's process: 18/01258-5 - Novel chemical catalytic and photocatalytic processes for the direct conversion of methane and CO2 to products
• Grantee: José Maria Correa Bueno
• Support Opportunities: Research Projects - Thematic Grants