Copper‐Catalyzed β‐Iodovinylation of Carbamates: Expedient Access to Highly Functionalized Vinyl‐Carbamates. Issue 17 (7th May 2018)

• Record Type: Journal Article
• Authors: Ricard, Simon; Gagnon, Alexandre; Daoust, Benoit
• Is Part Of: ChemistrySelect. Volume 3:Issue 17(2018)
• Page Start: 4923
• Page End: 4929
• Publication Date: 2018-05-07
• Subjects: Acyclic carbamates -- Copper catalysis -- Cross-coupling -- β-Iodovinyl carbamates -- N-Vinylation -- Vinyl carbamates; Chemistry -- Periodicals; 540.5
• DOI: 10.1002/slct.201800824
• Languages: English
• ISSNs: 2365-6549

Abstract

Abstract: A general and efficient method for the synthesis of β‐iodovinyl carbamates via copper‐catalyzed β‐iodovinylation of acyclic carbamates is described. This method uses readily available ( E )‐1, 2‐vinyl diiodides and regioselectively affords the corresponding β‐iodovinyl carbamates in good yields with complete stereocontrol of the alkene. Further functionalization of these versatile products leads to a wide diversity of β‐functionalized vinyl‐carbamates in good to excellent yields. Abstract : Copper‐catalyzed β‐iodovinylation of acyclic carbamates using ( E )‐1, 2‐vinyl diiodides afforded the corresponding β‐iodovinyl carbamates in good yields with complete regio‐ and stereocontrol of the olefin. Further functionalization led to a wide diversity of β‐functionalized vinyl‐carbamates in good to excellent yields.