Rh(I)-catalyzed ring-opening of cyclobutanols via C–C bond activation: Synthesis of cis-olefin with a remote aldehyde. Issue 39 (27th September 2019)

• Record Type: Journal Article
• Authors: Nie, Yu; Chen, Jianzhong; Zhang, Wanbin
• Is Part Of: Tetrahedron. Volume 75:Issue 39(2019)
• Publication Date: 2019-09-27
• Subjects: C–C bond activation -- Ring-opening -- Cyclobutanols -- cis-Olefin -- Remote aldehyde; Chemistry, Organic -- Periodicals; 547.005
• DOI: 10.1016/j.tet.2019.130563
• Languages: English
• ISSNs: 0040-4020

Abstract

Abstract: A Rh(I)-catalyzed ring-opening of cyclobutanols has been developed with ring opening products bearing cis- olefin and a remote aldehyde. Various substrates bearing different substituted aryl groups, heterocyclic groups and alkyl groups were compatible with the mild reaction conditions. A β -C elimination pathway was proposed based on the results of preliminary mechanistic studies. Graphical abstract: Image 1 Highlights: The substrates are easy to synthesize. An efficient method to obtain Z -alkenes in high selectivity. The products can be easily transformed to other useful compounds. A β -C elimination pathway was proposed.