Alkene‐Zipper Catalyzed Selective and Remote Retro‐ene Reaction of Alkenyl Cyclopropylcarbinol. Issue 7 (13th February 2018)

• Record Type: Journal Article
• Authors: Bruffaerts, Jeffrey; Vasseur, Alexandre; Marek, Ilan
• Is Part Of: Advanced synthesis & catalysis. Volume 360:Issue 7(2018)
• Page Start: 1389
• Page End: 1396
• Publication Date: 2018-02-13
• Subjects: Remote functionalization -- retro-ene -- Ruthenium -- Mechanistic investigation -- Catalytic alkene isomerization.; Catalysis -- Periodicals; Organic compounds -- Synthesis -- Periodicals; Chemistry -- Periodicals; Chemistry, Technical -- Periodicals; Chemistry -- Periodicals; Catalysis -- Periodicals; Technology, Pharmaceutical -- Periodicals; 547.2
• DOI: 10.1002/adsc.201701481
• Languages: English
• ISSNs: 1615-4150

Abstract

Abstract: Reminiscent of biological systems, the increasingly popular concept of remote activation allows a greater strategic synthetic flexibility for the development of novel synthetic organic methodologies. In this Communication, we report that commercially available ruthenium (II)‐based "alkene zipper catalyst" enables the selective transformation of a large variety of ω‐alkenyl cyclopropylcarbinols into stereodefined unconjugated ( E )‐acyclic aldehydes bearing a quaternary stereocenter through an isomerization followed by a retro‐ene reaction. To unravel this peculiar catalytic property of the "alkene zipper" and shed some light on the mechanism, a series of control experiments were performed. Abstract :